Vacation rentals in Leesburg, FL with free parking

Explore 102 vacation rentals, homes, and villas with free parking in Leesburg, FL for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $71 per night and homes offering up to 4 bedrooms and 3 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

102 Homes with Free Parking in Leesburg

Walk to Restaurants: Downtown Leesburg Townhome!

Leesburg, FL, US
3 Bedrooms 6 Guests
Aug 23 - 26
$132 night

Looking for a relaxing escape to Central Florida? Bring your family or friends to this 3-bedroom, 2-bath Leesburg vacation rental! The townhome has all the essentials, including a full kitchen and a deck. Plus, you'll be within a 12-mile radius of several golf courses and plenty of parks and trails! -- THE PROPERTY -- SLEEPING ARRANGEMENTS: - Bedroom 1: King Bed - Bedroom 2: Queen Bed - Bedroom 3: Queen Bed INDOOR LIVING: - Smart TV w/ cable - Dining table, breakfast bar - Laptop workspace OUTDOOR LIVING: - Furnished balcony & deck - Dining area KITCHEN: - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics - Drip coffee maker, microwave, toaster, ice maker GENERAL: - Free WiFi - Central A/C & heating, ceiling fans - Linens/towels - Iron/board - Complimentary toiletries - Trash bags, paper towels, hair dryer FAQ: - Exterior security camera (facing out) ACCESSIBILITY: - Step-free entry, 1st-floor bedroom PARKING: - Driveway (1 vehicle) - Free street parking (first-come, first-served) -- THE LOCATION -- - 8 miles to Sharon Rose Wiechens Preserve & Lake Okahumpka Park - 45 miles to Orlando - 5 miles to Leesburg International Airport & 55 miles to Orlando International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this property features step-free entry and 1 bedroom located on the 1st floor, the remaining bedrooms are located on the 2nd floor and require stairs to access - NOTE: Your safety matters. This property features an exterior security camera located on the front of the property facing toward the front entry area. This camera does not look into any interior spaces. This camera records sound and video when activated by motion and will be on during your stay

Fechtel’s Oasis – Your Gateway to The Villages

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 31 - Sep 5
$101 night

IMPORTANT BEFORE BOOKING: ☀️ January through April require full-month bookings. 📅 February reservations are only available when combined with a January stay (February cannot be booked alone). ☀️ Inquire for Monthly Discounts May–October! Guests who book 30+ nights during these months are eligible for exclusive rates—ask us for details! ☀️ Fechtel’s Oasis – Your Gateway to The Villages & Beyond (Newell) A Bright & Breezy Getaway in The Villages – Near Golf, Fun & Magic! 🌴 3BR/2BA | Golf Cart Community | Fully Equipped Kitchen | Near Golf & Rec Centers | Within direct reach of the Florida Turnpike Welcome to Fechtel, your ideal home base in the charming Village of Newell—The Villages’ newest and most exciting neighborhood! Whether you’re here to unwind, explore, golf, or dive into nonstop activities, this bright and cheerful cottage offers the perfect blend of comfort, convenience, and Florida fun. 🏡 Home Highlights: Comfort, Space & Style This 3-bedroom, 2-bath cottage-style home is designed to make you feel right at home: • Master Bedroom – Plush king bed, spacious layout, closet, and natural light • Guest Bedroom 1 – Queen bed and comfortable décor, perfect for guests or adult family • Guest Bedroom 2 – Two twin beds, great for kids, friends, or extra flexibility • Living Room – Cozy seating and TV for relaxing after your adventures • Fully Equipped Kitchen – Everything you need for meals at home, including cookware, coffee maker, and more • Laundry Room – In-unit washer/dryer for your convenience • Wi-Fi and Cable TV included 🐶 Dog-Friendly: Bring your furry companion! We welcome one well-behaved dog—please inquire for approval prior to booking. ⛳ Golfers’ Paradise Just minutes from Mickylee Pitch & Putt, Jubilee Putting Course, and Southern Oaks Championship Course, Fechtel is the perfect launchpad for golf lovers. With a Villages guest ID, you’ll also have access to 40+ Executive Courses included with your stay! 🏊‍♀️ Franklin Recreation Center – A Must-Visit Just around the corner from Fechtel, Franklin Rec Center is your go-to hub for indoor and outdoor fun: • Indoors: Billiards, ping pong, Xbox consoles, table shuffleboard, darts, and card rooms • Outdoors: Shuffleboard courts, outdoor exercise equipment, a refreshing family pool, and golf nearby • It’s a favorite gathering spot with a friendly, social atmosphere You’ll also be near the Homestead Recreation Area, featuring an astronomy observation pad and a dedicated dog park! 🎶 Nightly Live Entertainment & Events Easily head to: • Sawgrass Grove – The Villages’ exciting new hot spot with live music, boutique shopping, and delicious dining • Lake Sumter Landing, Brownwood, and Spanish Springs – Each with free nightly live music, dancing, bars, and entertainment every day of the year • Special Events: St. Patrick’s Day Parade, Rocky Fest, Craft Fairs, and more! 🎢 Easy Access to Florida Attractions Thanks to quick access to the Florida Turnpike, day trips to Orlando are a breeze! • Walt Disney World – ~75 minutes • Universal Orlando & SeaWorld – ~1.5 hours • Orlando International Airport (MCO) – ~1 hour Your sunny getaway is ideally located for magic and memories beyond The Villages. 🌿 Nature, Trails & Outdoor Fitness • Stroll or bike the Hogeye Preserve Pathway and explore shaded trails, nature lookouts, and peaceful walking paths • Visit dog parks, enjoy picnic areas, and take part in outdoor classes like Zumba, yoga, cardio drumming, and tai chi 🎨 Culture, Clubs & Community • See live performances at The Sharon Performing Arts Center or Studio Tierra Del Sol • Enjoy local art at Artists ’Round The Square • Join one of 3,000+ clubs—from pickleball and poker to pottery and photography • Special programs include Camp Villages for visiting grandkids and the popular Senior Games 🛒 Dining & Shopping • Walk or cart to Sawgrass Grove for great eats, drinks, and boutique shopping • Stock up at Southern Trace Plaza, Publix, and local farmers markets • Medical, salon, and service essentials are all just minutes away 🚗 Getting Around • Golf Cart Friendly: Travel over 100 miles of scenic golf cart paths • Public Transit: Sumter County shuttles available • Drive Time: Quick access to Tampa, Orlando, and beyond via nearby highways 📌 Additional Details: Temporary Resident ID: $50 per person (paid directly to The Villages), allows access to all resident-only amenities. At least one guest must be 55+ per The Villages’ community requirements. 🌞 Fechtel Cottage – Your Gateway to Fun, Sun & Florida Living Whether you’re relaxing with your pup, golfing all day, dancing under the stars, or soaking up the local arts and events, Fechtel offers the perfect blend of tranquility and adventure in one of the most active, welcoming communities in the U.S. 🎉 Book your stay today and come experience everything The Village of Newell has to offer—from local charm to world-class entertainment!

Home w/ Lanai + Community Perks in The Villages!

Leesburg, FL, US
3 Bedrooms 6 Guests
Sep 30 - Oct 4
$175 night

This 3-bedroom, 2-bathroom vacation rental located in The Villages features all the fun-filled amenities you could wish for. Discover nearby recreation centers, pools, and golf courses galore! This recently constructed home is decked out with new decor, appliances, and furnishings. You’ll love taking your morning coffee on the shaded and breezy screened-in private lanai, and you’ll never want to leave the deluxe bedroom suite, which features a walk-in closet and a roomy en-suite bathroom. -- THE PROPERTY -- Gated 55+ Community | Golf Cart Available for Guest Use | Screened-In Private Lanai | Resort-Style Amenities | Shower Seat Bedroom Suite: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed COMMUNITY AMENITIES (pass required): 38 executive golf courses, 12 Championship Courses w/ 306 holes, 100+ swimming pools, 100+ recreation centers, tennis courts, horseshoes, cornhole, archery, volleyball courts, croquet, shuffleboard, bocce courts, basketball courts, nature trails, fishing, dog park, pickleball courts, astronomy park, billiards, darts, card room, meeting rooms OUTDOOR LIVING: Patio, grill, dining area, lounge furniture, private yard, pond view, golf cart available for guest use INDOOR LIVING: 2 Smart TVs, new furnishings, contemporary decor, dining area, en-suite bathroom w/ dual-sink vanity, walk-in closet KITCHEN: Stainless steel appliances (stove/oven, fridge, microwave, dishwasher), blender, coffee maker, cooking basics, dishware & flatware, toaster, starter pack of coffee, breakfast bar GENERAL: Keyless entry, complimentary toiletries, free WiFi, central A/C & heat, hair dryer, trash bags & paper towels, linens & towels, washer/dryer, laundry detergent FAQ: 1 exterior Ring doorbell camera (facing front entry) ACCESSIBILITY: Single-story home, half step to enter, grab rails in shower PARKING: Garage (2 vehicles), driveway (2 vehicles) -- THE LOCATION -- STROLL THE VILLAGES: Homestead Recreation Center (0.3 miles), The Villages Astronomy Viewing Pads (0.3 miles), The Market at Sawgrass Grove (2 miles), Ezell Regional Recreation Center (2 miles), St. Catherine Postal & Neighborhood Recreation Center (2 miles), Cason Hammock Postal & Recreation (2 miles) OPT OUTSIDE: Lake Okahumpka Park (7 miles), Flat Island Preserve (9 miles), Lake Griffin State Park (12 miles), Lake Miona Park (14 miles), Dade Battlefield Historic State Park (20 miles), Lake Weir (21 miles), Carney Island Recreation & Conservation Area (28 miles), Silver Springs State Park (35 miles) AREA ATTRACTIONS: Brownwood Paddock Square (8 miles), Paquette’s Historical Farmall Museum (8 miles), Lake Sumter Landing Market Square (11 miles), Spanish Springs Town Square (14 miles), Uncle Donald’s Farm (16 miles), Grand Oaks Resort Carriage and Museum (17 miles), Disney World (46 miles), GatorWorld Parks of Florida (52 miles) TEE OFF: Mickylee Pitch & Putt (0.5 miles), Southern Oaks (2 miles), Belle Glade Golf & Country Club (7 miles), Sarasota Golf Practice Center (8 miles), Bonifay Golf & Country Club (8 miles), Evans Prairie Golf and Country Club (9 miles), Truman Executive Golf Course (9 miles) AIRPORTS: Orlando International Airport (54 miles), Tampa International Airport (84 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 35 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The single-story home requires a half step to enter and features grab rails in the shower - NOTE: This property is located within a 55+ community. Other guests in the party do not need to be 55+ as long as one 55+ booking guest is present - NOTE: Villages Lifestyle IDs and Villages Guest IDs are both available to guests upon request. Lifestyle IDs grant full access to amenities, including all executive courses and all pitch and putt golfing, and you can book tee times; this is $50 for 2 Lifestyle IDs (max 2). Guest IDs are free and grant access to all recreational pools and facilities; however, there is still a small fee to access certain amenities like golf and tennis, and you cannot book tee times - NOTE: Guests who reside within Lake, Sumter, and Marion Counties are eligible for 2 Lifestyle IDs but are not eligible for Guest IDs - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed

Premier View (Dabney - The Enclave)

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 23 - 28
$142 night

February and March require a full month booking. Premier View Residence – Entertainment & Elegance at The Enclave Welcome to Premier View Residence, a luxurious and fully furnished retreat in The Enclave at Villages of Dabney, designed for the perfect vacation experience. Nestled in a serene location with nature views and modern amenities, this premier home blends comfort, entertainment, and convenience, making it an exceptional choice for your stay in The Villages. 🌟 About the Home This brand-new, 3-bedroom, 2-bathroom premier home is thoughtfully furnished to cater to all your needs: King bed in the master suite, with large windows showcasing stunning nature views and custom walk-in closet systems. Master bathroom with dual sinks/cabinetry and dual shower heads. Queen bed in the second bedroom and a working den, ideal for remote work or leisure. Modern kitchen with quartz countertops, stainless steel appliances, a 5-burner stove, and a spacious pantry. An open floor plan with luxury vinyl plank flooring, tile bathrooms, and high 10-foot ceilings for an airy feel. Oversized sliding doors opening to a large backyard with tranquil views of the preserves. Living room with a 75" TV and comfortable seating for cozy evenings. TVs in all bedrooms (50" in master, 43" in guest rooms) for personalized entertainment. A dining table that converts to a pool or ping pong table, perfect for group fun. Additional features include stadium chairs for enjoying live music at the town squares and floaties and towels for pool adventures. The 2-car garage and golf cart garage ensure ample parking, electric charging station and storage space for your convenience. 🏞️ Explore The Villages & Nearby Attractions Located in the Villages of Dabney, this home offers unparalleled access to: Sawgrass Market Square: Enjoy live entertainment, delicious dining, and a vibrant social scene year-round. Franklin & Ezell Recreation Centers: Featuring lap pools, pickleball courts, and countless activities. Dabney Pool: A relaxing spot for sun-soaked afternoons. Southern Oaks Championship Golf Course: A premier golfing destination just minutes away. Magnolia Plaza: For all your retail needs, including groceries, pharmacy, restaurants, Foxtail Coffee, and 7-Eleven. 🎶 The Villages Lifestyle As a guest, immerse yourself in the active and vibrant community of The Villages: Over 40 Executive Golf Courses and championship courses, accessible with your Villages ID. Daily live music at the town squares, with events, festivals, and endless entertainment options. Recreational opportunities including lap pools, water volleyball, pickleball, and platform tennis. Convenient proximity to the Florida Turnpike and retail shopping in nearby Leesburg. This home is not only a tranquil retreat but also a gateway to all The Villages has to offer. With its ideal location, modern design, and entertainment-focused amenities, Premier View Residence provides the ultimate short-term rental experience. Book now and make unforgettable memories in this exceptional home! Pet Policy Small, non-shedding dogs (1 dog per stay) are welcome. No cats allowed.

Mickylee Pond & Golf View Retreat at Lake Denham

The Villages, FL, US
3 Bedrooms 6 Guests
Oct 31 - Nov 5
$142 night

🌴 Mickylee Pond & Golf View Retreat at Lake Denham 🌴 Welcome to Mickylee Pond & Golf View Retreat at Lake Denham, a beautiful 3-bedroom, 2-bathroom designer home that perfectly blends comfort, privacy, and The Villages’ signature active lifestyle. Enjoy breathtaking views of both the pond and the Mickylee Pitch & Putt course — right from your own backyard! This home offers the ideal balance between tranquility and convenience — peaceful mornings with water and golf course views, and afternoons filled with entertainment, recreation, and dining just minutes away. 🏡 Home Features 3 Bedrooms, 2 Bathrooms — Spacious designer layout filled with natural light and comfortable furnishings. Master Suite — King-size bed, large TV, walk-in closet, and ensuite bathroom with dual sinks and a walk-in shower. Guest Bedroom #2 — Features a queen-size bed and plenty of closet space. Guest Bedroom #3 — Includes two twin beds, perfect for visiting family or friends. Living Room — Bright and welcoming with a large-screen TV, ideal for relaxing after a day of fun. Kitchen — Fully equipped and beautifully furnished with everything needed for home-cooked meals, entertaining, or enjoying breakfast with a pond and golf view. Outdoor Space — A fully fenced backyard overlooking both the pond and the Mickylee Pitch & Putt, offering peace, privacy, and a front-row seat to The Villages lifestyle. Garage — Two-car garage for your convenience. This home is fully furnished and move-in ready, designed to make your stay comfortable and effortless. 🌳 Neighborhood & Nearby Attractions Located in the sought-after Villages of Lake Denham, this home sits in one of the most scenic and active areas in the southern Villages. Mickylee Pitch & Putt – Just steps away, offering an enjoyable and scenic round of golf right outside your back door. Franklin Recreation Center – Less than a mile away, with both indoor and outdoor recreation. Dabney Recreation Center & Homestead Recreation Center – About a mile to a mile and a half away, each with family and adult pools, pickleball, bocce, and more. Sawgrass Grove – Only about 2 miles away, featuring nightly live music, restaurants, retail shops, and entertainment. Eastport Square – Opening late 2025 to early 2026, bringing new restaurants, entertainment, and community spaces to the area. You’ll also be within golf-cart distance of multiple executive and championship golf courses, recreation centers, and The Villages’ best walking and biking trails. 🏓 Recreation & Lifestyle Recreation in Lake Denham covers everything from indoor fun to outdoor adventures: Indoor amenities: Ping pong Billiards / pool tables Video game and media areas Outdoor amenities: Bocce ball Shuffleboard Pickleball courts Tennis courts Outdoor walking and fitness trails Whether you prefer relaxing by the pool, joining a recreation class, or playing a round of golf, there’s always something to enjoy nearby. 🏷️ Guest Access & Policies Guests can obtain Temporary Resident IDs from The Villages for a $50 fee (paid directly to The Villages). These passes provide access to 40+ executive golf courses, all recreation centers, and community pools. 🐾 Dogs allowed upon approval 🚫 No cats permitted 🚭 No smoking or vaping inside the home ☀️ Why You’ll Love Mickylee Pond & Golf View Retreat Wake up to stunning water reflections and peaceful views of the Mickylee Pitch & Putt. Spend your afternoons golfing, relaxing by the pool, or enjoying live music and dining at Sawgrass Grove. Mickylee Pond & Golf View Retreat at Lake Denham offers the best of The Villages — comfort, views, and a true Florida lifestyle in one perfect location.

Pam Place Bliss Villa

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 28 - Sep 2
$95 night

Beautiful NEW villa in a very ACTIVE side of town. You have lots of WALKING TRAILS, walking distance to the Mickylee Pitch and Putt, and the Franklin Recreation Center with the POOL, pickleball, tennis and LOTS OF GAMING activities to pick from. Less than a mile and a half you have the Homestead Recreation Center and close by is the Ezell Recreation, and SAWGRASS for fun!!! And the list is long if we add all the other amenities, rec centers and squares you can visit in The Villages. This beautiful brand new 2 bed / 2 bath is in The Village of Lake Denham. This villa has beautiful new furniture from Babette’s Furniture and Decor, and it has a FULLY EQUIPPED kitchen, linens, towels, etc. It has a BBQ grill for your use. Your washer and dryer are inside for your convenience, and you have a COZY PORCH to sit outside to appreciate the sunlight with your cup of coffee in the morning. WIFI, CABLE TV, ACCESS TO STREAMING. A lot of sitting areas, a dining TABLE FOR SIX, THREE STOOLS in the kitchen, and a seating area in the PORCH. You will LOVE this property. With your booking you will receive a DIGITAL GUIDE with all the details about the property, ebike rentals discounts, and recommendations of places to visit. By the time you arrive, your Lifestyle ID will be waiting for pick up at the Brownwood Paddock Square sales office (you will be asked for identification and a $50 payment) so you can start enjoying all the amenities The Villages has to offer. This is a very active area where you see lots of neighbors outside, walking, riding bicycles, running. The Villages is an Active 55+ Community. Young visitors are allowed for limited periods with plenty of family activities.

Draper Villa Getaway (Lake Denham)

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 23 - 28
$89 night

🌴 Draper Villa Getaway — Modern Comfort & Central Florida Access in The Villages Welcome to Draper Villa Getaway, a stylish and well-situated 2-bedroom, 2-bath villa located in the desirable Village of Lake Denham—just steps from the fun and amenities of Dabney Recreation Center and minutes from The Villages’ vibrant southern corridor. Whether you’re looking for an extended seasonal stay or a long-term rental, this home offers the comfort, convenience, and access you’re looking for. 🛏️ Cozy & Comfortable Layout • Two private bedrooms, master with a king-sized bed and guest bedroom has a queen bed for restful sleep • Open-concept living and dining space, perfect for relaxing or entertaining • Fully equipped kitchen, in-home laundry, and a screened lanai for breezy mornings or winding down in the evening 🎾 Endless Amenities at Your Doorstep Located just around the corner from the Dabney Recreation Center, you’ll enjoy easy access to: Adult swimming pool, pickleball courts, and fitness trail Peaceful walking and biking areas Close proximity to the beautiful Franklin Recreation Center and expansive Homestead Recreation Center, which offer additional pools, bocce, shuffleboard, and indoor activities 🎶 Minutes from Sawgrass Grove & Eastport Entertainment Your villa is a quick golf cart ride to Sawgrass Grove, a major hub for food, fun, and live music every night. Explore: EZELL Regional Recreation Complex with a state-of-the-art gym and sports courts McGrady’s Pub, food vendors, and artisan market-style eateries Live nightly entertainment on the Sawgrass stage And just across the Brexley Bridge via McNeil Drive, Eastport’s recreation and dining options are quickly coming to life, adding even more vibrancy to the area 🛣️ Prime Central Florida Location • Quick access to Leesburg for shopping, restaurants, and medical services • Close to Florida’s Turnpike and Highway 44 for easy travel around the region • Just 55 minutes to Walt Disney World and major Orlando attractions • Within 30–45 minutes of multiple natural springs (Silver Springs, Alexander Springs, Juniper Springs, and more) for kayaking, tubing, and hiking adventures • Under 90 minutes to both Atlantic and Gulf Coast beaches 📅 Flexible Rental Options Available for both short-term and long-term stays, Draper Villa is ideal for snowbirds, travel professionals, or anyone exploring The Villages lifestyle. 🛺 Golf Cart Rentals Available Let us connect you with trusted golf cart rental providers to make getting around even more enjoyable. 💸 Seasonal Discounts Ask about special weekly or monthly discounts available from June through October for extended summer stays.

Queen Dabney Villa

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 23 - 28
$85 night

☀️ Welcome to Queen Dabney Villa – Your Fresh, Fun Florida Escape in The Villages! Come soak up the Florida sunshine at Queen Dabney Villa, a beautifully decorated, newly built 2-bedroom home located in one of the most exciting and up-and-coming areas of The Villages. Whether you’re looking to relax poolside, cruise the trails, hit the golf course, or enjoy live music and great food, this villa puts you right where the fun begins. 🛏️ Comfortable & Relaxing Spaces Master Bedroom: King-size bed, en-suite bathroom, and a spacious walk-in closet Guest Bedroom: Queen-size bed with tasteful décor and plenty of storage Plush bedding, premium towels, and everything you need to feel at home 📺 Entertainment & Chill Time TVs are available in the Living Room and Master Bedroom so you can kick back and enjoy your favorite shows after a day of adventure. ☕ Easy Mornings & Relaxing Evenings Start your day with coffee from the Keurig on the front porch, taking in the peaceful breeze and sunshine. Wind down in the evenings with a cold drink and the tranquil ambiance of this quiet neighborhood. 🍳 Fully Equipped Kitchen Enjoy the freedom to cook in your fully stocked kitchen, complete with modern appliances and all the essentials to prepare your favorite meals or quick bites. 🚲 Explore with Ease A four-seater golf cart is available for use, making it easy to explore nearby recreation centers, pools, and entertainment Two bicycles with helmet are also available—perfect for cruising along the scenic trails and exploring the natural beauty surrounding the neighborhood 🏊‍♂️ Endless Fun at Nearby Recreation Centers Dabney Recreation Center (within minutes!) Adult pool Pickleball & tennis courts Shuffleboard, bocce, and outdoor games Walking trails and peaceful green spaces Franklin Recreation Center Family-friendly pool Additional courts and outdoor sports facilities Gathering spaces and community activities Homestead Recreation Center Large fitness pool and sports courts Meeting and hobby rooms A great space to enjoy both indoor and outdoor activities Other neighborhood recreation centers nearby also offer family pools, fitness trails, sports, and fun programming year-round. ⛳ Golfer’s Paradise If you’re a golfer, you’re in for a treat! Nearby and easily accessible: Mickylee Pitch & Putt – Perfect for fun, casual play in a social setting Southern Oaks Championship Golf Course – One of the premier courses in The Villages 40+ Executive Golf Courses throughout the community – Access included with your Temporary Resident ID (small cart fees apply) All reachable by golf cart! 🎟️ Temporary Resident ID – Your Key to The Villages For just $50 per couple (paid directly to The Villages), guests can obtain Temporary Resident IDs, which unlock: Access to all pools (adult, family, sports) Use of 40+ executive golf courses Entry to recreation centers and participation in thousands of activities and clubs Access to priority tee times, fitness classes, pickleball, tennis, arts & crafts, and so much more! A true pass to live like a Villager during your stay! 🛍️ Close to the Action – Now and Coming Soon! Already Open: Booster Grill and Victory Grill have opened in Eastport, bringing in great food and local energy—perfect for casual bites, watching the game, or meeting new friends Coming Soon – Just a Short Drive Away: The brand-new, state-of-the-art Eastport Town Square is set to begin opening in Winter 2025 Expect restaurants, entertainment, a hotel, and beautiful waterfront settings — sure to be one of the most exciting places in all of The Villages 🐶 Pet Policy Dogs allowed upon approval No cats allowed 🌞 Make Your Florida Stay Shine Whether you’re here to unwind, explore, socialize, or play, Queen Dabney Villa delivers a fun, active, and easygoing Florida experience. With nearby pools, golf, trails, and the buzz of Eastport on the rise — this villa is the perfect launchpad for your next Villages adventure.

Salty Kisses Villa at The Villages (Edenfield)

Sumterville, FL, US
2 Bedrooms 4 Guests
Sep 30 - Oct 2
$108 night

Salty Kisses Villa | Walk to Edenfield Pool | Minutes to Eastport & Sawgrass Grove Welcome to Salty Kisses Villa, a charming and beautifully appointed 2-bedroom, 2-bathroom retreat located in the highly desirable Village of Edenfield, one of the most exciting and fastest-growing areas of The Villages. This cozy villa offers the perfect combination of comfort, convenience, and location. Whether you’re coming to enjoy pickleball, nightly entertainment, golf cart adventures, or simply relaxing by the pool, Salty Kisses Villa places you in the center of it all. 🏡 The Home Designed with a comfortable split-bedroom floor plan, the villa provides privacy and space for couples, friends, or seasonal guests. Sleeping Arrangements Primary Suite with King Bed Guest Bedroom with Queen Bed Split floor plan for added privacy Bathrooms Primary Ensuite featuring a walk-in shower Guest Bathroom with tub/shower combination Living Area Comfortable reclining chair Large Smart TV Bright and inviting living room Open-concept design perfect for relaxing after a day of exploring Kitchen & Dining Fully equipped kitchen with everything needed for cooking and entertaining Dining table and cozy dinette area All cookware, dishes, utensils, and kitchen essentials included Additional Amenities All linens provided Bath towels provided Pool towels provided Garage access Two bicycles available for guest use Bicycle helmets included Folding chairs for enjoying live music at the town squares and special events 🌊 Unbeatable Location One of the best features of Salty Kisses Villa is its location. Walk to Edenfield Pool The neighborhood pool is just a short 2-3 minute walk from your front door, making it easy to enjoy a morning swim or relax in the Florida sunshine. Quick Access to Eastport & Sawgrass Grove Within minutes you’ll have access to the Bexley Trail, providing easy access to the vibrant Eastport and Sawgrass Grove areas. Enjoy: Live entertainment Outdoor dining Specialty meat market Mediterranean cuisine Healthy food options Ice cream shop Pizza restaurant Burger restaurant Coffee shop Weekly events including popular Boozy Bingo nights Seasonal festivals and community events 🎾 Recreation & Sports Nearby you’ll find some of the newest and most sought-after recreation facilities in The Villages. Eastport Recreation Area State-of-the-art amenities Walking and biking trails Beautiful outdoor gathering spaces Olympia Recreation Center One of the newest and most impressive recreation centers in The Villages featuring: Pickleball courts Tennis courts Indoor and outdoor activities Advanced fitness facilities Sports programming Unique indoor climbing features and recreational spaces Franklin Recreation Center A short distance away and home to: Additional pickleball courts Tennis courts Adult pool Recreation programs and classes You’ll also enjoy easy access to nearby pools and recreation centers throughout: Edenfield Well Point Oak Hollow Dabney Middleton area neighborhoods 🚲 Explore The Villages Bring your sense of adventure. Enjoy scenic rides through some of the newest and most beautiful areas of The Villages. Downtown Eastport The newest town center featuring: Waterfront-inspired design Rooftop dining experiences Live music Unique shopping Entertainment venues Ice cream and coffee shops Exciting events throughout the year Downtown Middleton Just minutes away and home to: The Morse Restaurant Community gathering spaces Family-friendly events Beautiful parks and walking areas Brownwood Paddock Square Approximately a 20-minute golf cart ride away. Enjoy: Nightly live music Restaurants and bars Shopping Farmers markets Festivals and events Along the way, stop at local favorites including: Harry and The Natives for daily entertainment and refreshments Waterfront dining locations Scenic golf cart routes through some of the most beautiful areas of The Villages 🐾 Pet-Friendly We know vacations are better with your best friend. Salty Kisses Villa is dog-friendly (with approval) and conveniently located near: Dog parks Walking paths Nature trails Pet-friendly outdoor dining areas Open green spaces perfect for daily walks Why Guests Love Salty Kisses Villa ✔ Walk to the Edenfield Pool ✔ Minutes from Eastport and Sawgrass Grove ✔ King Bed + Queen Bed ✔ Split Floor Plan ✔ Fully Equipped Kitchen ✔ Large Smart TV ✔ Bikes Included ✔ Pool Towels Included ✔ Pet-Friendly ✔ Access to Some of the Newest Amenities in The Villages Whether you’re escaping the cold, exploring The Villages lifestyle, or simply looking for the perfect Florida getaway, Salty Kisses Villa offers an unbeatable combination of comfort, location, and fun. We look forward to welcoming you!

Hawkins Azure Pool Home

Wildwood, FL, US
3 Bedrooms 6 Guests
Aug 31 - Sep 5
$243 night

🌴 Hawkins Azure Pool Home – Luxury Retreat in the Heart of The Villages 🌴 ✨ Immerse yourself in the ultimate Florida lifestyle at Hawkins Azure Pool Home — a beautifully appointed 3-bedroom, 2-bathroom villa designed for comfort, elegance, and effortless access to all The Villages has to offer. Nestled in the highly desirable Hawkins neighborhood, this home combines modern living with the charm of community-centered recreation, shopping, dining, and entertainment. 🏡 Thoughtful Interior Comfort Primary Suite: King-size bed dressed in luxury linens, large walk-in closet, and a private en-suite bath. Guest Room 1: Queen bed, perfect for visiting friends or family. Guest Room 2: Murphy bed for flexible sleeping arrangements or to use as an office/flex space. Chef’s Kitchen: Fully equipped with high-end appliances, spacious counters, and everything you need to entertain or prepare meals with ease. Relaxing Living Area: Comfortable open layout with large TV, soft seating, and natural light. 🌿 Outdoor Living & Entertaining Step out onto the spacious screened lanai overlooking a beautifully landscaped yard. Perfect for: Morning coffee or sunset cocktails Al fresco dining with friends Reading and relaxing in your private outdoor space. The Hawkins neighborhood pool is just moments away — a heated pool where you can enjoy a daily swim or unwind under the Florida sun. 🏌️‍♂️ Prime Location – Close to Everything! Hawkins offers the best of The Villages’ southern lifestyle: 🚲 Minutes by golf cart to Sawgrass Grove — a lively destination with nightly entertainment, excellent dining, and retail shops. 🍽️ Steps away from McGrady’s Pub (live music, hearty meals, and community feel). 🛍️ Close to Magnolia Plaza and Lake Deaton Plaza, featuring Publix, retail shops, pharmacies, banks, and other conveniences. 🏖️ Just a short golf cart ride to Brownwood Paddock Square — enjoy free nightly live music, restaurants, boutique shops, and events. 🏸 Recreation & Active Living Hawkins Pool: Heated neighborhood pool perfect for daily swims and relaxation. Everglades Recreation Center: One of the largest in The Villages, featuring pickleball courts, tennis, bocce, walking trails, outdoor sports areas, and community events. Aviary Recreation Center: Resort-style experience with family-friendly activities and fitness amenities. Golf lovers: You’re surrounded by 40+ executive courses and championship courses within golf cart distance. 🆔 Guest Access & Amenities Guests may request a Temporary Resident ID ($50 fee paid directly to The Villages), unlocking access to: 40+ executive golf courses (no greens fees) Championship golf courses (reduced resident rates) All recreation centers, pools, fitness facilities, and events across The Villages. Nightly live entertainment at all three main squares: Brownwood, Lake Sumter Landing, and Spanish Springs. 👉 Golf carts are the preferred way to get around — everything is within easy carting distance from this home! 🌟 The Lifestyle From morning walks on nature trails to sunset happy hours at Sawgrass Grove, this home places you right in the middle of The Villages’ vibrant lifestyle. Whether your passion is golf, live music, dancing, dining, fitness, or simply relaxing in the Florida sunshine, Hawkins Azure Pool Home makes it all effortless. 📅 Book your seasonal stay today and make your Florida retreat unforgettable.

The Villages Home w/ Golf Cart & Community Pools!

Wildwood, FL, US
2 Bedrooms 4 Guests
Aug 31 - Sep 2
night

Soak up the Florida sun and treat yourself to a stay in this 2-bedroom, 1-bath vacation rental in The Villages! Boasting a fully equipped kitchen, a cozy living space, an outdoor patio with a grill, and plenty of community amenities, this lovely home sits in a quiet, gated neighborhood offering all the peace and relaxation you desire! Wander along the nature trails at Lake Okahumpka, hit the links for a round, explore Spanish Springs Town Square, or simply spend the day relaxing at the pool. -- THE PROPERTY -- Bedroom 1: Queen Bed | Bedroom 2: Twin Bed w/ Twin Trundle COMMUNITY AMENITIES: Neighborhood outdoor pool (adults only), family outdoor pool at the Aviary recreation center (all ages), bocce, corn toss, darts, meeting room, outdoor pavilion, pickleball court, tennis court, shuffleboard OUTDOOR LIVING: 2-person golf cart (waiver may be required), beach towels, patio w/ seating, gas grill (propane provided) INDOOR LIVING: Dining table, ceiling fans, Smart TV, cable, games, bar cart KITCHEN: Breakfast bar, refrigerator, microwave, stove/oven, dishwasher, dishware/flatware, coffee maker, toaster, ice maker, trash bags/paper towels GENERAL: Keyless entry, central air conditioning, complimentary toiletries, hair dryer, iron/board, linens/towels FAQ: Step-free access PARKING: Garage (1 vehicle), driveway (1 vehicle), no street parking, no campers/boats/large vehicles allowed in the driveway -- THE LOCATION -- THINGS TO DO: Magnolia Plaza (2 miles), Brownwood Paddock Square (7 miles), Lake Sumter Landing Market Square (10 miles), Spanish Springs Town Square (12 miles), Uncle Donald’s Farm (15 miles), Grand Oaks Resort (16 miles) GOLFING: Southern Oaks Championship Golf Course (1 mile), Lowlands Executive Golf Course (4 miles), Red Fox and Gray Fox Executive Golf Course (5 miles), Belle Glade Golf & Country Club (6 miles), Sarasota Golf Practice Center (6 miles) DAY TRIP: Universal Studios (45 miles), Orlando (46 miles), Walt Disney World Resort (51 miles), Tampa (76 miles), Daytona Beach (101 miles) OUTDOOR RECREATION: Aviary Village Recreation Center (1 mile), Ezell Regional Recreation Center (1 mile), Lake Okahumpka Park (5 miles), Lake Griffin State Park (11 miles), Lake Panasoffkee (16 miles), Silver Springs State Park (34 miles) AIRPORTS: Orlando International Airport (56 miles), Tampa International Airport (84 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: A waiver may be required prior to using the golf cart

Denver Corner Villa at The Villages

The Villages, FL, US
2 Bedrooms 4 Guests
Sep 22 - 27
$102 night

Denver Corner Villa | Stylish Lanai • 4 Seater Golf Cart • Near Sawgrass Grove & Eastport in The Villages, FL Experience the very best of Florida living at **Denver Corner Villa**, a beautifully maintained two-bedroom, two-bath corner villa located in the highly desirable **Village of Lake Denham** on the growing south side of **The Villages®, Florida**. Perfectly positioned near **Sawgrass Grove, Eastport, and Brownwood Paddock Square**, this inviting home offers comfort, convenience, and easy access to some of the newest dining, golf, recreation, and entertainment in The Villages. Designed for relaxation and memorable stays, this immaculate villa is ideal for both short-term getaways and extended stays in one of Florida’s most sought-after active lifestyle communities. The bright, open-concept floor plan creates a welcoming atmosphere with comfortable furnishings throughout. The living room is perfect for unwinding after a day of exploring The Villages, featuring a large TV and two plush recliners—ideal for movie nights, sports, or relaxing evenings at home. The fully equipped kitchen includes everything you need to prepare meals, including cookware, dishes, coffee maker, blender, crockpot, toaster, and everyday essentials. The spacious primary suite offers a comfortable king-size bed, TV, large walk-in closet, and a private ensuite bathroom with a walk-in shower. The guest bedroom features a queen-size bed and is conveniently located next to the second full bathroom, which includes a bathtub—perfect for visiting family or friends. One of the standout features of this home is the beautifully extended lanai. This outdoor living space includes both covered and open seating areas, making it the perfect place to enjoy morning coffee, afternoon cocktails, or evening gatherings. Watch football, concerts, or your favorite shows on the outdoor big-screen TV while enjoying Florida’s year-round sunshine. ### Home Features & Amenities * Complimentary high-speed Wi-Fi * Central air conditioning * Full-size washer and dryer * TVs in the living room and primary bedroom * Outdoor big-screen TV on the lanai * Folding chairs for nightly entertainment at The Villages town squares During your stay, you’ll also enjoy a **4-passenger golf cart**, allowing you to easily explore The Villages using its extensive golf cart trail system—one of the most unique features of this community. Nature lovers will appreciate the peaceful surroundings of Lake Denham, including scenic walking trails, ponds, and opportunities for bird watching right in the neighborhood. ### Recreation Centers & Nearby Attractions Just minutes away is **Franklin Recreation Center**, offering: * Resort-style family pool * Pickleball courts * Tennis courts * Mickey Lee Pitch & Putt Golf Course You’ll also be close to **Homestead Recreation Center**, featuring: * Additional pickleball courts * Dog park * Astronomy Park * Year-round recreational activities and events ### Sawgrass Grove – Dining, Entertainment & Events A short golf cart ride brings you to **Sawgrass Grove**, one of the newest and most popular entertainment destinations in The Villages. Here you’ll find live entertainment nearly every day of the year, including the popular **Boozy Bingo on Mondays**, along with: * Casual dining options * Burgers and pizza * Coffee shop and ice cream * Meat market and convenience grocery * Indoor and outdoor bars * Beautiful gathering spaces * Adjacent Regional Recreation Center with year-round activities ### Eastport – The Newest Destination in The Villages Just across the Turnpike bridge is the exciting and rapidly growing **Eastport area**, one of the newest hubs in The Villages. Enjoy: * Waterfront views and scenic walking paths * New restaurants, bars, and shopping * Live entertainment throughout the year * Access to golf courses, recreation centers, and pools * Beautiful architecture and vibrant community spaces ### Additional Dining & Entertainment Nearby You’ll also be conveniently located near: * **Boosters Bar & Grill** * **Harry & the Natives** overlooking the water * **Brownwood Paddock Square** (approximately 30 minutes by golf cart), offering nightly live entertainment, restaurants, shopping, and one of the most popular town squares in The Villages Whether you’re visiting The Villages for golf, pickleball, live music, dining, or simply relaxing in the Florida sunshine, **Denver Corner Villa** provides the perfect home base in a prime location near everything you want to experience. ### Pet Policy One well-behaved dog may be considered with prior approval. Please contact us before booking if you plan to travel with a dog. Cats are not permitted. ### Golf Cart Disclaimer A 4-passenger golf cart is provided as a convenience for registered guests. Prior to use, all drivers must sign the required Golf Cart Waiver. Drivers must be at least the minimum required age, possess a valid driver’s license, and operate the golf cart responsibly and in accordance with all applicable laws and community rules. Operation of the golf cart while under the influence of alcohol or any impairing substance is strictly prohibited. AJ Home Rentals, AJ Home Concierge, and the property owner assume no responsibility for accidents, injuries, damages, traffic violations, or losses resulting from the use of the golf cart. Additional terms and conditions apply and are included in the Golf Cart Waiver.

Ruhlman Pool & Preserve Retreat in The Villages

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 23 - 28
$210 night

Welcome to Ruhlman Pool & Preserve Retreat, a peaceful and beautifully appointed home designed for comfort, relaxation, and enjoying the sunny Florida lifestyle. Located on a desirable corner lot with serene preserve views in the Villages of Lake Denham, this inviting retreat combines the privacy of a quiet setting with the fun and convenience of everything The Villages has to offer. With a private pool, spa, heater available, and a lovely enclosed lanai, this home is the perfect place to enjoy morning coffee, poolside afternoons, and relaxing evenings after a day of golf, dining, or exploring the area. Whether you’re here for a seasonal stay, a getaway, or an extended visit, Ruhlman Pool & Preserve Retreat is a warm and welcoming place to call home during your time in The Villages. 🛏 Bedrooms & Bathrooms 2 Bedrooms | 2 Bathrooms Primary Suite Comfortable King bed Private en-suite bathroom Spacious layout Designed for restful, relaxing stays Guest Bedroom Comfortable Queen bed Bright and welcoming atmosphere Easy access to the nearby guest bathroom Ideal for couples, friends, seasonal guests, or anyone looking for a comfortable and well-appointed home base. 🛋 Living & Indoor Comfort The interior of the home is designed to feel cozy, open, and easy to enjoy. Comfortable living room seating Large TV for relaxing evenings Open dining area Fully equipped kitchen with essentials for cooking and entertaining Kitchen bar seating for casual meals, coffee, or conversation The home has a warm and easy flow that makes it ideal for both short and extended stays. 🌿 Outdoor Living — The Ruhlman Experience This home truly shines in its outdoor spaces. Enjoy your own private Florida retreat with: ✔ Private pool ✔ Spa / hot tub ✔ Pool heater available ✔ Enclosed lanai ✔ Peaceful preserve views ✔ Ping pong table for added fun ✔ Outdoor seating for morning coffee and relaxing evenings The combination of the preserve backdrop and the pool/spa setting makes this home feel especially relaxing and private. Whether you’re spending the afternoon in the pool, enjoying the spa in the evening, or simply unwinding on the lanai, this is the kind of space guests truly enjoy. 🐾 Pet Policy Dogs allowed with prior approval only No cats permitted Please inquire before booking for approval. 💃 Temporary Resident ID & Amenity Access Guests staying at Ruhlman Pool & Preserve Retreat are eligible to obtain a Villages Temporary Resident ID (available for a $50 fee paid directly to The Villages). With this Temporary Resident ID, guests can enjoy: Access to 40+ Executive Golf Courses Courses suitable for all skill levels Use of many recreation centers, pools, activity spaces, and amenities The opportunity to fully experience the active and social Villages lifestyle during your stay 🎶 Town Centers, Dining & Entertainment 🎶 Sawgrass Grove One of the most popular nearby destinations, Sawgrass Grove offers a relaxed but lively atmosphere with: Multiple restaurants and casual dining options Outdoor gathering areas Live music most afternoons and early evenings Coffee, treats, and places to linger Boozy Bingo on Monday nights — always a guest favorite 🌟 Eastport Eastport is part of the surrounding Villages area and is approximately a 15-minute golf cart ride. Enjoy: Dining Events Live performances A growing and energetic entertainment area 💃 Brownwood Paddock Square A Villages favorite known for: Larger live music stages Nightly entertainment Great dining options Dancing and classic Villages square fun Live music is offered nightly throughout the Villages squares, making it easy to find something enjoyable every evening. 🍽 Dining Highlights (South of Ruhlman) The southern Villages area continues to grow and offers many great nearby options, including: Boosters Grill Fenney Grill Harry & the Natives / Harold’s at Lake Sumter Local spots near Sawgrass and Eastport Whether you’re looking for casual dining, outdoor seating, or a fun evening out, there are plenty of options nearby. 🏌️ Recreation Centers & Active Lifestyle 🏓 Franklin Recreation Center Located nearby and full of activities, Franklin offers: Mickey Lee Pitch & Putt Golf Course Pickleball courts Bocce ball Ping pong Pool tables Many additional recreational opportunities 🐕 Homestead Recreation Center Approximately 1 mile from Franklin, Homestead offers: One of the largest dog parks in the area An Astronomy Park Resort-style pool Pickleball and bocce Shuffleboard and organized activities 💙 Why Guests Love Ruhlman Pool & Preserve Retreat • Private pool and spa • Pool heater available • Beautiful preserve views • Peaceful corner-lot location • Enclosed lanai for added comfort • Ping pong table for extra fun • Great location close to golf, dining, recreation, and nightly entertainment • Warm, welcoming, and ideal for enjoying The Villages lifestyle

Home in The Villages Near the Newer Town Centers!

Wildwood, FL, US
2 Bedrooms 4 Guests
Sep 30 - Oct 14
$173 night

Leave all of your worries at home and relax in the Florida sunshine at this vacation rental! This 2-bedroom, 2-bathroom villa offers a lovely interior, with a fully equipped kitchen and access to tons of community amenities around The Villages. Perfect your swing at the many nearby golf courses or soak up some sun at one of the nearby pools. There is always something going on in the town squares… live music, special events, farmers markets, and after a day out, sip a cocktail on the lanai. -- THE PROPERTY -- Pet Friendly w/ Fee | Lanai | Free WiFi | Beach Towels | Perfect Location Bedroom 1: King Bed | Bedroom 2: King Bed | Living Room: Sleeper Sofa COMMUNITY AMENITIES (additional fee, paid on-site): Outdoor pools, hot tubs, tennis, bocce & pickleball courts, shuffleboard, cornhole, golf courses, fitness centers, recreation centers, nature trails INDOOR LIVING: 2 Smart TVs, 6-person dining table, en-suite, walk-in closet, board games KITCHEN: Fully equipped w/ stainless steel appliances, breakfast bar w/ seating, coffee maker, toaster, Nutri-Bullet, spices, cooking basics, dishware/flatware GENERAL: Central A/C & heating, linens & towels, washer/dryer, complimentary toiletries, ceiling fans, hair dryer, hangers, trash bags & paper towels FAQ: 1 step required for access, pet fee (paid pre-trip), golf cart in garage not available PARKING: Driveway (1 vehicle, 1 golf cart), garage (1 vehicle) -- THE LOCATION -- OUTDOOR FUN: Hawkins Pool (0.6 miles), Everglades Recreational Center (1.5 miles), Homestead Recreational Center (2.6 miles), Fenney Recreational Center (3.9 miles), Brownwood Paddock Square Regional Town Center (4.8 miles), Sawgrass (1.9 miles), Eastport Recreation Center ( 3.8 miles), Sharon Rose Wiechens Preserve (5.9 miles), Lake Griffin State Park (10.0 miles), Lake Sumter Landing (10.2 miles), Spanish Springs Town Square (14 miiles). HIT THE LINKS: Southern Oaks by Ezell Recreation Center (1.8 miles), Woodlands Champion Golf 4.3 miles) Honeysuckle, Beautyberry, Bellaire, Grey Fox and Red fox are great executive golf courses and Par 3 courses…too many to mention! Country clubs like Havana Golf and Country Club ( 7.1 mikes) Palmer Legends Country Club (11.2 miles), Hacienda Hills Golf & Country Club (12.6 miles) and a ton of other golf courses by new area of Eastport! DAY TRIPS: Disney World ( 58 miles); Universal Studios (49.1 miles), Orlando (49.4 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - Pet friendly w/ $125 fee (+ fees & taxes, max 2 pets) - No smoking - Pet friendly w/ $100 fee (+ taxes & fees, max 2) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Community amenities are available for an additional on-site fee. More information on the community amenities will be provided before your stay - NOTE: The golf cart located in the garage is not available for guest use Licence number: DWE7000508

Phifer’s Paradise Cozy Cottage (Newell)

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 23 - 28
$85 night

🌴 Welcome to Phifer’s Paradise – Your Cozy Cottage Getaway in The Villages! 🏡 Located in the heart of The Villages, Florida’s most vibrant 55+ active adult community, Phifer’s Paradise is your cheerful, comfortable home base in the charming Village of Newell. This 2-bedroom, 2-bath dog-friendly cottage is perfect for golfers, nature lovers, and anyone ready to experience The Villages lifestyle at its finest! 🏡 Home Highlights 2 Bedrooms / 2 Bathrooms – ideal for couples, friends, or family Master Bedroom with King Bed and private ensuite Guest Bedroom with cozy Queen Bed Spacious Living Room with a flat-screen TV—great for relaxing or movie nights Fully Equipped Kitchen with all the essentials for meals at home Dog Friendly – one small dog welcome (inquire for approval before booking) Walkable to Golf – enjoy casual rounds at Mickylee Pitch & Putt, just steps away! 🌟 Prime Location with Endless Activities You’re literally across the street from Franklin Recreation Center, one of the most exciting and activity-packed facilities in The Villages! Guests love being able to walk right over and enjoy: Pickleball Courts Tennis Courts Shuffleboard Bocce Ball Billiards & Ping Pong Outdoor Exercise Stations Family Pool ...and much more—all just a few steps from your front door! In addition, you’re just minutes away from: Homestead Recreation Center, featuring: An adult-only pool Dog park Outdoor fitness stations Stargazing pads at the Astronomy Park Additional pickleball courts, trails, and activities ⛳ Golfer’s Paradise Mickylee Pitch & Putt – walkable, no tee time needed Jubilee Putting Course – fun and accessible Southern Oaks Championship Course – a short golf cart ride away 40+ Executive Courses – accessible with a $50 Temporary Resident ID (per couple) from The Villages, providing access to: Executive Golf Recreation Centers Pools And more! Golf cart not included, but we’re happy to refer you to trusted local rental vendors. 🎶 Entertainment Around Every Corner Sawgrass Grove – 5-minute golf cart ride away for: Nightly live music McGrady’s Pub Indoor market & boutique shopping Dancing, dining, and events under the stars Brownwood Paddock Square & Lake Sumter Landing Free nightly concerts Restaurants, retail, & seasonal festivals Over 3,000 clubs & activities in The Villages: Pickleball, crafts, fitness, photography, and more! 🌿 Nature, Trails & Wildlife Explore preserved nature areas surrounding Newell Hogeye Preserve Trail nearby for scenic walking, jogging, or bird watching Shaded paths and serene lakes make every walk peaceful and refreshing 🛍️ Shopping, Dining & Everyday Needs Magnolia Plaza – just a few minutes away with: Publix Supermarket Gas station Restaurants, salons, and essential services Additional shopping plazas and retail centers within golf cart range 🚗 Perfect for Day Trips & Adventure Easy access to the Florida Turnpike Great base for visiting: Disney World, Universal Studios, SeaWorld Natural springs like Rainbow Springs, Silver Springs, and Crystal River 📅 Extended Stay Discounts Looking to stay longer? Ask us about special monthly rates from May through October—a fantastic option for snowbirds or remote workers seeking sunshine and serenity. 🎉 Your Village of Newell Adventure Starts at Phifer’s Paradise! Whether you’re teeing off in the morning, lounging by the pool at Franklin Rec, strolling through nature preserves, or dancing the night away at Sawgrass Grove, this charming cottage home puts you right in the heart of everything The Villages has to offer. Let your Newell story begin—book your stay at Phifer’s Paradise today!

Fun & Sun in The Villages: 2BR Home w/ Lanai

Fruitland Park, FL, US
2 Bedrooms 4 Guests
Aug 23 - 25
$120 night

30+ Golf Courses Nearby | Dog Friendly w/ Fee | Fully Stocked Kitchen The Villages delivers year-round sunshine, world-class golf, and a resort lifestyle unlike anywhere else — and this vacation rental is your home base for it all. In between active outings, the home’s airy interior gives you a comfortable space to reset, while the lanai adds an open-air perch for coffee and evening drinks. Reserve this home now and tee off in one of Florida's most iconic communities! -- THE PROPERTY -- COMMUNITY AMENITIES - Outdoor pool - Golf courses, rec centers HOME HIGHLIGHTS - TVs, dining table - Washer & dryer - Lanai, lounge seating & outdoor dining KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Keurig - Cooking basics, dishware & flatware ACCESSIBILITY - Single-level home, step-free access PARKING - Garage (2 vehicles) - Driveway (2 vehicles) -- THE LOCATION -- - 1 mile to Okeechobee Executive Golf Course - 4 miles to Lake Sumter Landing Market Square: dining, live music, shopping - 5 miles to Brownwood Paddock Square: restaurants, boutiques, entertainment - 13 miles to Eaton's Beach - 5 miles to Target & 4 miles to Walmart -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes, dogs only, max 2 allowed) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM to 8:00 AM

Jessica’s Heated Pool Eastport Retreat (LaGrange)

The Villages, FL, US
3 Bedrooms 5 Guests
Oct 31 - Nov 29
$143 night

Brand-New Corner Cottage Home in The Villages | 3 Bedrooms | 2 Bathrooms | 4-Seat Golf Cart Included 2 Mins from Eastport | 8 Mins to Sawgrass Welcome to Jessica’s Eastport Retreat at Villages of LaGrange, a beautifully decorated, brand-new corner cottage home ideally located in the exciting new Eastport area of The Villages®. Designed for comfort, relaxation, and fun, this stunning home comfortably accommodates up to six guests and places you in the heart of the fastest-growing and most exciting area in The Villages. Step inside and enjoy a bright, open-concept floor plan featuring all-new furnishings, tasteful décor, and a fully equipped kitchen that flows seamlessly into the dining and living areas. Whether you’re preparing a meal, entertaining friends, or simply relaxing after a day of activities, you’ll feel right at home. The spacious primary suite features a comfortable king-size bed, while the two guest bedrooms each offer queen-size beds, providing comfortable accommodations for family and friends. The dining area seats six, and the inviting lanai offers a peaceful space to enjoy your morning coffee or unwind with an evening cocktail. A four-seat golf cart is included, making it easy to explore everything The Villages has to offer. Exceptional Eastport Location One of the home’s greatest features is its location. You are just a short walk from the spectacular Olympia Recreation Center, one of the newest and most impressive recreation facilities in The Villages. This state-of-the-art complex features indoor pickleball courts, a climbing wall, fitness areas, gathering spaces, and a wide variety of activities and events. Eastport itself has quickly become one of the most sought-after destinations in The Villages. The area offers beautiful landscaping, scenic pathways, and unique larger-than-life sculptures celebrating sports and recreation, creating fun photo opportunities throughout the district. You’ll also enjoy easy access to: Multiple family and adult pools Pickleball courts Tennis courts Walking and biking paths Championship golf courses Numerous executive golf courses Recreation centers offering activities for every interest Minutes from Sawgrass Grove Just a short golf cart ride away is the popular Sawgrass Grove, one of the newest entertainment destinations in The Villages. Here you’ll find: Live music and entertainment nightly Boozy Bingo on Mondays Casual and upscale dining options Outdoor and indoor bars Pizza, burgers, and comfort food Mediterranean cuisine Coffee shops Ice cream shops A specialty meat market Healthy grocery selections Beautiful gathering spaces and outdoor seating Explore Magnolia Plaza & Everglades Recreation Center Nearby Magnolia Plaza offers convenient shopping and services including: Publix Restaurants Nail salon Hair salon Barbecue restaurant Everyday conveniences The nearby Everglades Recreation Center provides another incredible destination for activities, sports, pickleball, tennis, clubs, and events throughout the year. Easy Access to Brownwood Paddock Square Take a scenic golf cart ride to Brownwood Paddock Square, where you’ll enjoy: Live entertainment 365 days a year Restaurants and bars Shopping Dancing Festivals Special events The famous Brownwood atmosphere that has become a favorite gathering place for residents and visitors alike Additional Information Village Resident Lifestyle IDs are available for purchase directly through The Villages and provide access to many of the community’s amenities, recreation centers, executive golf courses, pools, and activities. This home is not pet friendly and has never housed pets, making it an excellent choice for guests with allergies or sensitivities. Home Features 3 Bedrooms / 2 Bathrooms King Bed in Primary Suite Queen Bed in Guest Bedroom #1 Queen Bed in Guest Bedroom #2 Sleeps Up to 6 Guests Brand-New Furnishings & Décor Open-Concept Living Area Fully Equipped Kitchen Dining Seating for 6 Comfortable Lanai Seating Corner Lot Location 4-Seat Golf Cart Included Non-Smoking Property No Pets Allowed Come experience the newest and most exciting area of The Villages while enjoying all the comforts of home at Jessica’s Eastport Retreat.

Tucson Trail Retreat

The Villages, FL, US
3 Bedrooms 5 Guests
Aug 23 - 28
$118 night

Lanai has been furnished - Pictures coming soon! 🏡 Fully Furnished Lanai & Stunning Water Views – Your Perfect Retreat on Tucson Trail! 🌟 Experience the ultimate blend of comfort, nature, and elegance in this breathtaking 3-bedroom, 3-bathroom home located in the Villages of Lake Denham. Wake up to serene pond views right from your bed and soak in the beauty of Florida’s premier active community. 🌟 Thoughtful Design & Elegant Furnishings This home is beautifully appointed with designer furniture and a fully furnished lanai—perfect for morning coffee, evening relaxation, or simply enjoying the peaceful water views. (Photos coming soon!) 🛏️ Spacious & Comfortable Bedrooms Master Suite – King-sized bed, TV, en-suite bathroom, and breathtaking water views right from your bed. Second Bedroom – Cozy queen-sized bed for restful nights. Third Bedroom – Another queen-sized bed, ideal for family or guests. 🌿 Nature Lover’s Paradise on Tucson Trail! Nestled in one of the most scenic areas of The Villages, this home offers access to some of the best nature trails—perfect for walking, cycling, and nature photography. Whether you’re capturing Florida’s stunning wildlife or enjoying peaceful strolls, the natural beauty surrounding Lake Denham is truly unmatched. 🌴 Explore The Villages from Lake Denham Living in the Villages of Lake Denham means you’re close to some of the best amenities The Villages has to offer: 🎶 Sawgrass Grove Entertainment – Enjoy live music, delicious dining, and social events in this lively community hub. 🏊 Ezell Recreation Center – Featuring pools, pickleball courts, and a variety of activities to keep you active and entertained. ⛳ Southern Oaks Championship Golf Course – A golfer’s paradise just minutes away, offering a world-class golfing experience. 🚶 Scenic Walking & Biking Trails – The area is perfect for outdoor lovers, offering peaceful nature trails, lakeside views, and bird-watching opportunities. 🛍️ Shopping & Dining – Conveniently located near Colony Plaza, Magnolia Plaza, and other top shopping destinations, so you’ll have everything you need just a short golf cart ride away. 🚗 Convenience & Lifestyle 2-car garage + golf cart garage for easy access to The Villages’ countless amenities. Prime location near shopping, dining, and entertainment hubs, making every day feel like a vacation. 📅 Available Now – January, February & March 2026 Require Full-Month Booking! Don’t miss out on this incredible retreat in The Villages. Contact us today to schedule a viewing and make this stunning home yours!

Degarmos Comfy Villa at The Villages

Sumterville, FL, US
2 Bedrooms 4 Guests
Sep 30 - Oct 5
$114 night

Degarmos Comfy Villa at The Villages | New Pet-Friendly Villa Near Eastport Welcome to Degarmos Comfy Villa at The Villages, a beautifully appointed new 2-bedroom, 2-bathroom villa located in the Village of La Grange, one of the newest and most desirable areas of The Villages. Perfectly situated near Eastport, Olympia Recreation Center, championship golf, pools, pickleball courts, dining, entertainment, and miles of golf cart and bicycle paths, this home offers the perfect blend of comfort, convenience, and location. Whether you’re planning a seasonal stay, an extended Florida escape, or simply looking to experience the unmatched Villages lifestyle, Degarmos Comfy Villa provides everything you need to feel right at home. The Home This brand-new villa features a spacious open-concept layout with modern furnishings, thoughtful touches, and plenty of room to relax and entertain. Sleeping Arrangements King bed in the private master suite Queen bed in the guest bedroom Split floor plan for added privacy Master suite located at the rear of the home Guest bedroom and guest bath located toward the front of the home Smart TV in the master bedroom Living & Dining Comfortable reclining seating Large Smart TV in the living room Bright and spacious open kitchen Fully equipped kitchen with everything needed for short or extended stays Generous counter space for cooking and entertaining Dining table perfect for meals, games, and gatherings Outdoor Living Private screened lanai Outdoor dining table and chairs Privacy wall behind the home for a more secluded setting Perfect spot for morning coffee or relaxing after a day of activities Additional Features Golf cart garage Driveway parking High-speed Wi-Fi Washer and dryer Pet friendly (dogs upon approval, no cats) Discover Eastport – The Villages Newest Destination One of the biggest advantages of staying at Degarmos Comfy Villa is its proximity to Eastport, the newest and fastest-growing lifestyle destination in The Villages. Just minutes away, Eastport offers: Rooftop dining experiences Restaurants and casual eateries Coffee shops and cafés Ice cream shops Live music and daily entertainment Movies and special events Beautiful waterfront gathering areas Public art and walking paths Exciting new attractions and community activities You’ll also be a short ride from Sawgrass Grove, one of the area’s most popular gathering spots, featuring: Multiple restaurants Bars and social spaces Pizza and burger favorites Coffee shop Ice cream shop Specialty grocery and market offerings Live music Weekly activities and community events Recreation Everywhere Guests will enjoy access to some of the newest and most impressive amenities in The Villages. Nearby you’ll find: Multiple adult-only pools Family-friendly pools Championship golf courses Executive golf courses Pickleball courts Tennis courts Walking trails Scenic golf cart and bicycle paths The impressive Olympia Recreation Center is just minutes away and features: Indoor pickleball courts Fitness facilities Rock climbing wall Organized classes and activities Social events throughout the year With several recreation centers and pools within a short distance of the home, you’ll never run out of ways to stay active and connected. Explore The Villages and Central Florida Degarmos Comfy Villa offers easy access to everything that makes Central Florida special. Conveniently located near major roadways, guests can easily enjoy: Orlando attractions Tampa Bay attractions Florida’s beautiful natural springs Shopping, dining, and entertainment throughout Central Florida Golf Cart, Bicycle & Mobility Rentals While a golf cart is not included with the home, guests have easy access to local golf cart rental providers, bicycle rentals, and mobility scooter rentals. The home’s excellent location near Eastport, Olympia Recreation Center, and miles of pathways makes exploring The Villages easy and enjoyable. Lifestyle ID Access Guests may obtain Village Lifestyle IDs through The Villages, providing access to many recreation centers, pools, activities, and lifestyle amenities. Applicable Village fees apply. Additional guests may request guest passes to enjoy many of the area’s amenities during their stay. Why Guests Love Degarmos Comfy Villa ✓ Brand-new villa in one of The Villages newest neighborhoods ✓ King master suite with split floor plan ✓ Pet friendly (dogs upon approval) ✓ Private lanai with added privacy ✓ Fully equipped kitchen ✓ Golf cart garage ✓ Minutes from Eastport and Sawgrass Grove ✓ Close to Olympia Recreation Center ✓ Near multiple pools, golf courses, pickleball courts, and walking trails ✓ Easy access to Orlando, Tampa, and Florida’s natural springs Experience the excitement of Eastport, the comfort of a brand-new home, and the unmatched lifestyle that has made The Villages one of Florida’s most popular destinations. We look forward to welcoming you to Degarmos Comfy Villa at The Villages.

Community Pool & Tennis Court: Gem in The Villages

Leesburg, FL, US
3 Bedrooms 6 Guests
Aug 23 - 30
$181 night

Ensure plenty of entertainment for the entire family when you book this exciting vacation rental in The Villages! With a vibrant interior, fenced backyard, and access to incredible community amenities, this 3-bedroom, 2-bath house is perfect for a memorable stay in the Sunshine State. Tee off at nearby golf courses, enjoy the pickleball and tennis courts just down the road, or head out to explore surrounding nature preserves before retreating to unwind on the home’s furnished screened porch! -- THE PROPERTY -- In-Unit Laundry | Fenced Backyard | 8 Mi to Brownwood Paddock Square Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Sleeper Sofa | Additional Sleeping: Pack ‘n Play COMMUNITY AMENITIES: 2 outdoor pools, tennis & pickleball courts, shuffleboard, bocce, billiards room, darts, cornhole, astronomy pads INDOOR LIVING: Smart TV, dining table, walk-in closet, en-suite bathroom, ceiling fans OUTDOOR LIVING: Screened porch, patio seating KITCHEN: Refrigerator, coffee maker, stove/oven, microwave, dishwasher, dishware & flatware, cooking basics GENERAL: Keyless entry, self check-in, free WiFi, cable, central heating & A/C, washer & dryer, laundry detergent, towels/linens, trash bags/paper towels, complimentary toiletries ACCESSIBILITY: Single-story house, step-free access PARKING: Garage (2 vehicles), driveway (2 vehicles) -- THE LOCATION -- NEARBY ATTRACTIONS: Brownwood Paddock Square (8 miles), Venetian Gardens (10 miles), Lake Sumter Landing (12 miles), Swamp Fever Airboat Adventures (18 miles) OUTDOOR FUN: Lake Okahumpka Park (7 miles), Flat Island Preserve (8 miles), Pear Park Wildlife Conservation Area (8 miles), Lake Panasoffkee Refuge (14 miles) LOCAL GOLF COURSES: Mickylee Pitch & Putt (0.6 miles), Sandhill Executive Golf Course (11 miles), The Monarch at Royal Highlands (13 miles) DAY TRIPS: Walt Disney World (41 miles), Orlando (45 miles), Crystal River (49 miles) AIRPORTS: Leesburg International Airport (15 miles), Orlando International Airport (54 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story house offers step-free entry

Joseph’s Oasis at Dabney in The Villages

Okahumpka, FL, US
3 Bedrooms 5 Guests
Aug 23 - 28
$90 night

Joseph’s Oasis at Dabney 🌴 | Golf Cart Included | Near Sawgrass, Eastport & Nature Trails Escape to Joseph’s Oasis at Dabney, a beautifully appointed 3-bedroom, 2-bath villa nestled in one of the newest and friendliest neighborhoods in The Village of Dabney. Perfectly located in the exciting South Villages, you’ll enjoy the peaceful charm of a quiet residential street while being just minutes from recreation, entertainment, golf, dining, and everything that makes The Villages® one of Florida’s premier destinations. Whether you’re visiting to enjoy championship golf, pickleball, nightly entertainment, scenic nature trails, or simply relax in the Florida sunshine, Joseph’s Oasis is the perfect place to call home. 🏡 The Home This thoughtfully furnished villa comfortably accommodates up to six guests and offers an open, bright floor plan designed for relaxing after a day of exploring. Sleeping Arrangements 🛏️ Primary Suite King Bed Smart TV Private ensuite bathroom Double vanity Walk-in shower 🛏️ Guest Bedroom #2 Queen Bed Smart TV 🛏️ Guest Bedroom #3 Queen Bed Smart TV The guest bathroom features a bathtub/shower combination and is conveniently located between the guest bedrooms. 🍳 Fully Equipped Kitchen Whether you’re preparing a quick breakfast before golf or cooking dinner at home, you’ll find everything you need, including: ✔ Pots & pans ✔ Dishes and glassware ✔ Coffee maker ✔ Blender ✔ Crock Pot ✔ Toaster ✔ Cooking utensils ✔ Bakeware ✔ Plenty of countertop space …and much more. 🏠 Home Amenities ✔ High-speed Wi-Fi ✔ Smart TVs throughout the home ✔ Comfortable living room ✔ Washer & dryer in dedicated laundry closet ✔ Gas BBQ grill ✔ One-car garage ✔ Separate golf cart garage ✔ Spacious driveway accommodating two additional vehicles Everything has been prepared to make your stay comfortable, convenient, and worry-free. 🚗 Golf Cart Included One of the greatest ways to experience The Villages is by golf cart! This home includes a complimentary golf cart, allowing you to explore miles of golf cart paths connecting recreation centers, golf courses, restaurants, shopping, and entertainment. 🌴 Discover the South Villages Dabney Recreation Center Only about 5 minutes away by golf cart, you’ll enjoy: ✔ Resort-style pool ✔ Pickleball courts ✔ Tennis courts ✔ Bocce ✔ Recreation programs ✔ Daily community activities Franklin Recreation Center Approximately 10 minutes by golf cart, Franklin Recreation Center offers: ✔ The Mickey-themed Pitch & Putt Golf Course ✔ Family swimming pool ✔ Pickleball ✔ Tennis ✔ Indoor recreation activities ✔ Clubs and social events Homestead Recreation Center Just another few minutes beyond Franklin you’ll discover one of the area’s favorite recreation centers featuring: ✔ Adult pool ✔ Pickleball ✔ Tennis ✔ Astronomy Park ✔ Large & Small Dog Parks ✔ Beautiful walking trails ✔ Scenic Florida landscapes 🌿 Nature at Your Doorstep The Village of Dabney is surrounded by beautiful natural scenery. Take a morning or evening stroll along nearby walking trails where you’ll experience: Native Florida wildlife Peaceful ponds Beautiful birds Scenic marsh views Occasional sightings of Florida alligators from designated safe viewing areas It’s one of the most peaceful and beautiful areas in The Villages. 🎶 Sawgrass Grove Just minutes away by golf cart is the exciting Sawgrass Grove Entertainment District, one of the fastest-growing destinations in The Villages. Enjoy entertainment 365 days a year, including: 🎵 Live music 🎤 Music Bingo Mondays 💃 Dancing 🎉 Community events Restaurants include: 🍔 Burgers 🍕 Pizza 🥙 Mediterranean cuisine 🥩 Meat Market ☕ Coffee Shop 🍦 Ice Cream Shop 🥗 Healthy grocery selections 🍹 Indoor and outdoor bars Sawgrass Recreation Complex Adjacent to Sawgrass Grove is one of the largest recreation facilities in The Villages. Enjoy: ✔ Sports Pool ✔ Adult Pool ✔ Pickleball ✔ Tennis ✔ Putting Green ✔ Pool Tables ✔ Ping Pong ✔ Arts & Crafts ✔ Fitness classes ✔ Indoor clubs ✔ Daily recreation programs There’s always something happening. Eastport Cross the Turnpike bridge and within about 10 minutes by golf cart you’ll arrive at the exciting new Eastport entertainment district. Enjoy: ✔ Live entertainment every day ✔ Restaurants ✔ Shopping ✔ Beautiful waterfront atmosphere ✔ New recreation facilities ✔ Year-round events You’ll also be conveniently located near the growing Middleton Downtown area. Explore Even More Within a short drive you’ll also enjoy: 🚗 Brownwood Paddock Square 🚗 Lake Sumter Landing 🚗 Spanish Springs 🚗 Championship Golf Courses 🚗 Executive Golf Courses 🚗 Countless restaurants, shopping, and nightly entertainment Temporary Resident IDs (Highly Recommended) Guests staying 30 days or longer are eligible to purchase Temporary Resident IDs through The Villages. These IDs provide access to nearly everything residents enjoy, including: ✔ Executive golf courses (green fees apply) ✔ Recreation centers ✔ Adult and family pools ✔ Pickleball ✔ Tennis ✔ Bocce ✔ Recreation classes ✔ Hundreds of clubs and organized activities ✔ Resident-only amenities and events The current fee is approximately $50 per person (subject to change by The Villages). After your reservation is confirmed, AJ Home Rentals will send you the required forms and guide you through the application process so your IDs are ready shortly after your arrival. Pet Policy 🐶 Dogs may be considered with prior approval. Before booking, please send us: Breed Weight Age Number of dogs Additional pet fees may apply. Cats are not permitted. Unauthorized pets may result in additional cleaning or damage charges. Why Book with AJ Home Rentals? When you reserve with AJ Home Rentals, you’re choosing a locally owned and professionally managed company committed to providing a safe, seamless, and enjoyable experience. Our guests enjoy: ✔ Professionally cleaned and inspected homes ✔ Convenient self check-in ✔ Local guest support throughout your stay ✔ Responsive maintenance assistance when needed ✔ Assistance obtaining Temporary Resident IDs ✔ Carefully maintained homes ✔ Local knowledge and recommendations to help you make the most of your visit Our goal is to provide exceptional accommodations and outstanding service from the moment you book until the day you check out. 🚨 Golf Cart Disclaimer The golf cart is provided as a complimentary amenity for your convenience during your stay. By operating or riding in the golf cart, all guests acknowledge and agree that they do so entirely at their own risk. AJ Home Rentals, the property owner, and their respective employees, agents, contractors, and representatives shall not be held liable or responsible for any accident, injury, death, property damage, theft, citations, fines, losses, or claims arising from or related to the use or operation of the golf cart, regardless of cause. For the safety of all guests: Only licensed drivers who are 21 years of age or older may operate the golf cart. All passengers are required to wear seat belts at all times while the golf cart is in motion. Passengers must remain seated while the golf cart is moving. Drivers must obey all applicable Florida laws and The Villages community rules regarding golf cart operation. Guests are responsible for the safe operation, care, and security of the golf cart throughout their stay. Guests accept responsibility for any damage, misuse, missing items, or negligence occurring during their rental period. While we make every effort to keep the golf cart in excellent working condition, AJ Home Rentals and the property owner cannot guarantee its availability at all times. Should the golf cart become unavailable due to maintenance, mechanical issues, accidental damage, manufacturer recalls, weather events, or other circumstances beyond our control, our team will make every reasonable effort to diagnose the issue and restore the golf cart to service as quickly as possible. However, repair timelines may be affected by factors outside of our control, including the availability of replacement parts, mechanic scheduling, warranty requirements, weekends, holidays, or other service delays. Because the golf cart is provided as a complimentary amenity and is not part of the rental consideration, no refunds, credits, discounts, or other compensation will be issued if it becomes unavailable during your stay. We appreciate your understanding and patience should an unexpected issue arise, and we will always do our best to resolve the situation as promptly as possible. By completing your reservation and using the golf cart, you acknowledge that you have read, understood, and agree to the terms of this disclaimer. We look forward to welcoming you to Joseph’s Oasis at Dabney and helping you experience everything that makes The Villages one of Florida’s most unique and enjoyable destinations! 🌴☀️

Palm Paradise Villa

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 23 - 28
$91 night

🌴 Welcome to Palm Paradise Joseph Villa – Relax & Explore The Villages of Dabney! Your sun-soaked escape awaits at Palm Paradise Joseph Villa, a thoughtfully designed, brand-new retreat in the highly desirable Villages of Dabney. This charming villa captures the carefree spirit of Florida with its crisp white palette, palm-inspired décor, and welcoming layout—perfect for guests looking to relax and enjoy everything The Villages has to offer. 🛏️ Comfort Meets Style 2 Bedrooms / 2 Bathrooms Queen-sized bed in the tranquil master suite Two twin beds in the cozy guest room Walk-in closet in the primary bedroom for plenty of storage Remote-control ceiling fans and soft bedding for total comfort Safety grab bars in the master bathroom and shower for added support and ease 📺 Entertainment in Every Room Smart TVs in each room so everyone can unwind with their favorite shows Wi-Fi included for easy streaming or working remotely ☀️ Outdoor Vibes, Morning to Night Greet the morning with coffee on the inviting front porch Enjoy cocktails or dinner under the glow of palm tree lights BBQ grill available for delicious outdoor cookouts and casual dining 🍳 Fully Equipped Kitchen Modern appliances, cookware, coffee maker, and all essentials Whether you’re meal prepping or indulging in a local recipe, everything you need is here 🚴‍♂️ Explore The Villages with Ease 4-seater golf cart included* – perfect for exploring nearby town squares, trails, and pools Two cruiser bikes available for scenic rides and easy adventures Parking space for one car and the golf cart 🏞️ Activities & Entertainment Nearby You’re in the heart of Dabney and surrounded by fun! Dabney Recreation Center – Adult pool, pickleball, tennis, shuffleboard, bocce, and more Eastport Town Square – Just minutes away by golf cart! Enjoy live music, community events, shopping, and delicious dining options Sawgrass Market Place – McGrady’s Pub, live music, local produce, and vibrant nightlife Edna’s on the Green – A casual favorite for drinks, music, and a great social scene Fenney Grill – Local dining with warm atmosphere Everglades & Saluki Rec Centers – Pools, indoor fitness, pickleball, and nature paths Magnolia Plaza (~10 mins by golf cart) – Publix, gas station, dining, and soon-to-open CVS 🐾 Pet Policy One dog allowed upon approval – please reach out with details before booking 🚭 Other Policies No smoking or vaping indoors or on property ⚠️ Golf Cart Use Disclosure Use of the golf cart is permitted only for guests who sign a liability waiver. A&J Home Concierge is not a rental provider. Use is at your own risk. Only guests 25 years or older with a valid driver’s license may drive the golf cart. Seat belts must be worn at all times.

Timber Sunshine Stay (Villages of Dunedin)

The Villages, FL, US
3 Bedrooms 6 Guests
Nov 28 - Dec 3
$150 night

🌞 Timber Sunshine Stay | Designer 3-Bed Home in the Villages of Dunedin Welcome to Timber Sunshine Stay, a fully equipped designer home in the Villages of Dunedin, right in the heart of The Villages lifestyle. This comfortable and spacious home features: 3 bedrooms / 2 bathrooms One master bedroom with king-size bed, dresser, sofa, large TV, ensuite bathroom with walk-in shower, private toilet area, and walk-in closet Two guest bedrooms with queen-size beds and large wall closets TVs in both the master and living area Fully equipped kitchen for cooking and entertaining Breakfast nook with view of the kitchen Dining table ideal for meals, games, and puzzles Lanai with comfortable seating to enjoy coffee or a cocktail Spacious living room with two recliners and extra seating No carpet – only decorative area rugs for a clean, allergen-reduced environment Wi-Fi and Xfinity cable TV Dog-friendly (limit 1, non-shedding preferred – please inquire with pet details) 👉 This is the home for comfort, space, and great vibes—ideal for a seasonal escape or extended stay. 📍 Incredible Location – Everything Close By! Timber Sunshine Stay is strategically located with easy access to: Brownwood Paddock Square – Live music every night, shopping, dining, movie theater Lake Sumter Landing – More nightly entertainment, waterfront restaurants, retail shops Eastport – Newest addition to The Villages with event spaces and recreation Lake Deaton Plaza – Publix, Walgreens, banks, gas station Colony Plaza – Restaurants, salons, shopping, urgent care, and more Aldi & Walmart Neighborhood Market – About 10 minutes by car Eisenhower Recreation Center – One of the most popular centers with a military museum vibe Seabreeze and Lake Miona Rec Centers – Pools, pickleball, bocce, events, fitness Bonifay, Evans Prairie, and Palmer Legends Golf Courses – Championship golf nearby Dozens of Executive Golf Courses – All within a short ride Close to Meggison Road access and Southern Oaks Golf, making Eastport and the south end easily reachable 🏌️‍♀️ Guest Access to The Villages Amenities With Temporary Resident IDs ($50 per couple, paid directly to The Villages), you’ll enjoy: 40+ Executive Golf Courses with no green fees Resident access to Championship Courses at reduced rates Pools – family, adult, and sports pools Recreation Centers with hundreds of weekly organized activities Pickleball, Tennis, Bocce, Shuffleboard Nightly live entertainment at 3 different town squares Fitness trails, clubs, and much more! 📘 Digital Guidebook Provided After Booking You’ll receive a personalized Digital Guidebook including: Wi-Fi information Trash & pickup schedule Inventory and checkout checklist Golf cart rental contacts Restaurant and event recommendations The Villages event calendar Local attractions Children’s gear rental providers How to reach us during your stay And more! 🚭 No Smoking | 🐾 Dog-Friendly (with Approval) Non-smoking property – $500-$1000 fee for violations Pet Policy: Limit one dog, non-shedding preferred. Please inquire with breed and details before booking. Additional pet deposit may apply.

Haven on Earth | Luxury Pool Home at The Villages

Okahumpka, FL, US
3 Bedrooms 5 Guests
Aug 23 - 28
$210 night

Please send booking inquiries for approval first (December to April). February will require a January booking. Haven on Earth | Private Heated Pool & Spa • Designer Home • Golf Cart • Near Sawgrass, Eastport & Franklin Recreation Center Welcome to Haven on Earth, a one-of-a-kind designer home where every room tells a story. Located in the highly desirable Village of Lake Denham in The Villages, this beautifully appointed 3-bedroom, 2-bath home combines luxury, comfort, and playful vacation charm with an unforgettable coastal-inspired atmosphere. From the moment you arrive, you’ll notice this isn’t your typical vacation rental. Throughout the home you’ll discover carefully curated décor inspired by the sea, coastal living, and classic mythology. Elegant sculptures, artistic accents, whimsical treasures, and beach-inspired touches create a fun, memorable atmosphere that invites you to slow down, explore, and smile every time you look around. The décor is tasteful and unique—creating an experience that feels both relaxing and unlike anywhere else. Whether you’re planning a month of golf, sunshine, entertainment, or simply relaxing by your own private pool, Haven on Earth offers everything needed for an exceptional stay. 🏡 The Home This beautifully furnished Designer Home features: 3 Bedrooms 2 Bathrooms Private Heated Swimming Pool Private Heated Spa Spacious Screened Lanai 4-Seat Gas Golf Cart Included Full Laundry Room with Washer & Dryer Fast Wi-Fi Smart TVs Two-Car Garage Beautifully landscaped property The spacious open floor plan is perfect for relaxing after a day enjoying everything The Villages has to offer. The living room offers comfortable seating for everyone, centered around a large Smart TV, making it the perfect place to enjoy movie nights, sporting events, or simply unwind after a day by the pool. Natural light fills the home while coastal colors and thoughtfully selected artwork create a bright, welcoming atmosphere. 🍳 Fully Equipped Kitchen Whether preparing a quick breakfast before golf or entertaining family and friends, you’ll find everything you need, including: Fully stocked kitchen Keurig coffee maker Traditional drip coffee maker Toaster Blender Cookware Bakeware Full dinnerware Glassware Wine glasses Serving dishes Cooking utensils Microwave Dishwasher Full-size refrigerator Plenty of countertop workspace Everything has been thoughtfully prepared so you can cook just like home. 🛏 Sleeping Arrangements Primary Suite King Bed Smart TV Ensuite Bathroom Walk-in Shower Spacious closet Comfortable linens and premium bedding The primary suite provides a peaceful retreat overlooking the backyard. Ensuite Bathroom Walk-in shower Vanity Fresh towels Hair dryer Starter toiletries Guest Bedroom One Queen Bed Beautiful coastal décor Comfortable mattress Quality linens Guest Bedroom Two Queen Bed Bright and inviting Beautiful decorative touches Premium bedding Guest Bathroom Conveniently located between the guest bedrooms featuring: Tub/Shower combination Vanity Fresh towels Hair dryer 🌴 Your Private Backyard Oasis The backyard is where Haven on Earth truly shines. Enjoy your own private screened outdoor retreat featuring: Heated Swimming Pool* Heated Spa* Comfortable outdoor lounge seating Outdoor dining table with umbrella Conversation seating Private bar area One of the most charming features is the whimsical outdoor bar designed to resemble the iconic vintage Volkswagen camper van made famous by classic beach adventures—a perfect gathering spot for afternoon cocktails, evening conversations, or simply enjoying Florida’s beautiful weather. Surrounded by tropical landscaping and playful artistic accents, this backyard feels like your own private resort. *Pool and spa heat available for an additional fee. 🚗 Golf Cart Included Explore The Villages the way it was meant to be enjoyed. A 4-seat gas golf cart is included with your stay, allowing you to reach recreation centers, restaurants, golf courses, shopping, entertainment, and town squares using the community’s extensive golf cart trail system. 📍 Incredible Lake Denham Location One of the biggest advantages of Haven on Earth is its exceptional location in the rapidly growing southern area of The Villages. Franklin Recreation Center Just minutes away you’ll enjoy one of the newest recreation centers in The Villages featuring: Resort-style family pool Pickleball courts Tennis courts Bocce courts Cornhole Shuffleboard Indoor recreation rooms Table tennis Arcade-style games Social clubs Daily activities Arts and crafts Fitness programs Community events There is always something happening for every age and interest. Mickey Lee Pitch & Putt Located just around the corner, enjoy one of The Villages’ beautifully maintained Pitch & Putt courses—perfect for golfers looking for a relaxed and enjoyable round. Northside Recreation Complex Only about one mile away you’ll find another outstanding recreation destination offering: Adult swimming pool Additional pickleball courts Tennis courts Dog Park Astronomy Park Walking paths Recreation facilities Outdoor activities Sports courts Whether you’re bringing your clubs, your paddle, your telescope, or your walking shoes, Northside Recreation Center has something for everyone. 🛍 Sawgrass Grove Marketplace Just a quick golf cart ride away is one of the fastest-growing entertainment destinations in The Villages. Here you’ll enjoy: Live music every afternoon and evening Entertainment 365 days a year Restaurants Burger restaurant Pizza Mediterranean cuisine Coffee shop Ice cream shop Grocery market Fresh meat market Healthy food options Shopping Weekly events Outdoor seating Family-friendly atmosphere Even Mondays feature live entertainment, making Sawgrass one of the area’s favorite gathering places. 🌉 Easy Access to Eastport Cross the beautiful Bexley Trail Bridge, accessible by golf cart or car, and you’ll quickly arrive in the exciting new Eastport district. Within approximately 10 minutes you’ll enjoy: New restaurants Shopping Entertainment Scenic walking areas Championship golf Outdoor events New retail development Olympia Recreation Center Sports facilities Additional pools Recreation programs Eastport continues to grow and has quickly become one of the most exciting destinations within The Villages. 🎶 Explore Everything The Villages Has to Offer Using the included golf cart or your vehicle, you’ll also have easy access to: Brownwood Paddock Square (approximately 15 minutes) Lake Sumter Landing (approximately 20–25 minutes) Spanish Springs Town Square (approximately 30 minutes) Each town square offers nightly live entertainment, shopping, dining, dancing, and special events throughout the year. Included Amenities Heated Pool* Heated Spa* 4-Seat Gas Golf Cart High-Speed Wi-Fi Smart TVs Fully Equipped Kitchen Washer & Dryer Linens Bath Towels Beach/Pool Towels Hair Dryers Iron & Ironing Board Starter Supplies Driveway Parking Two-Car Garage *Additional fee applies for pool and spa heat. Resident Lifestyle ID Information Guests staying in The Villages may purchase temporary Resident Lifestyle IDs, which provide access to many of The Villages’ recreation centers, pools, executive golf courses (green fees apply), organized activities, clubs, and more. After your reservation is confirmed, we will send you a simple online form to complete with the names of eligible guests. Once submitted, we’ll prepare everything in advance so your IDs are ready for pickup upon arrival. The Villages currently charges $50 per household for temporary Resident Lifestyle IDs. This fee is set by The Villages and is subject to change without notice. Pet Policy Although this home is designed to be pet-friendly, pets are not permitted at this property. This helps us maintain the highest standards of cleanliness and comfort for all guests, including those with allergies. Please contact us if you have questions before booking. Golf Cart Disclosure A complimentary 4-seat gas golf cart is provided as a convenience during your stay. Guests operate the golf cart entirely at their own risk and are responsible for following all applicable laws, regulations, and The Villages community rules. Only licensed drivers may operate the golf cart. Guests are responsible for any citations, damages, towing charges, misuse, negligence, or loss occurring during their stay. Should the golf cart become unavailable due to maintenance, mechanical issues, accidental damage, manufacturer recalls, weather events, parts availability, or any circumstances beyond our control, no refunds, credits, or compensation will be provided. While every effort will be made to repair or replace the golf cart as quickly as possible, availability depends on service scheduling, parts, mechanics, and other factors outside our control. The golf cart is considered a complimentary amenity and is not part of the rental consideration. By using the golf cart, guests acknowledge and accept these terms. We appreciate your understanding and will always do our best to keep you enjoying everything The Villages has to offer.

Vacation Rentals in Leesburg by Amenities & Features

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What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Leesburg

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