Vacation rentals in Lady Lake, FL with free parking

Explore 55 vacation rentals, homes, and villas with free parking in Lady Lake, 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 Pet-Friendly Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $83 per night and homes offering up to 3 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.

55 Homes with Free Parking in Lady Lake

Avenida de las Casas – Spanish Springs Retreat

Lady Lake, FL, US
3 Bedrooms 6 Guests
Dec 31 - Jan 28
$259 night

Welcome to Avenida de las Casas, a stunning and incredibly unique 2,088 sq. ft. home featuring 3 bedrooms and 2.5 bathrooms. Perfectly located just steps from Spanish Springs Town Square, this residence blends elegance, comfort, and the signature Villages lifestyle all in one exceptional property. ✨ Main Level – Open & Elegant Living Step inside to a spacious, beautifully designed layout featuring a full primary suite on the first floor, offering both privacy and ease of access. The primary bedroom includes an en-suite bathroom and generous closet space, creating the perfect personal retreat. The open kitchen is truly the heart of the home — large, fully equipped, and perfect for cooking or entertaining. It opens into a comfortable living area with a large smart TV and access to streaming platforms, ideal for relaxing after a day of golf, shopping, or entertainment. A beautiful dining area with seating for eight adds a touch of elegance and sophistication, making it perfect for hosting dinners or enjoying memorable meals with family and friends. Just off the living room, step out to the lanai and garden patio — the perfect spot to enjoy the morning sun and the peaceful greenery. 🛏️ Upper Level – Private Guest Oasis Upstairs, two beautifully appointed guest bedrooms offer comfortable queen beds and plenty of natural light. A cozy den area upstairs provides a quiet corner for your morning coffee or reading time. Each bedroom features its own private balcony: Front balcony – offers charming water views between the nearby homes, ideal for enjoying morning sunrises or an evening breeze. Back balcony – overlooks the lush neighborhood greenery, offering a tranquil escape. This upper-level design creates a true sense of privacy and separation for guests or family. 🚗 Amenities & Extras 🛺 Two-seater golf cart included for easy access around The Villages. 🪑 Folding chairs provided to enjoy the live music at the squares. 🏊 Floaties available for the pools. 🧺 Fully equipped kitchen and laundry area. 🚻 Convenient half bath on the main floor for guests. 🏘️ Location – Steps from Spanish Springs You can’t get closer to Spanish Springs than this! Avenida de las Casas is walking distance to Spanish Springs Town Square, making it easy to enjoy: 🎶 Live music and dancing 365 days a year at the town square. 🍽️ A variety of restaurants, bars, cafés, and dessert shops. 🛍️ Local boutiques and major retail stores, including Publix, Walmart, and popular national brands just minutes away. ⛳ Immediate access to some of the best golf courses in the north end of The Villages, including Tierra Del Sol Country Club, Glenview Country Club, and executive courses such as El Diablo Executive Golf Course and El Santiago Executive Golf Course. 🏊 Close to multiple recreation centers and pools, with pickleball, tennis, bocce, shuffleboard, fitness, and daily activities nearby. 🆔 Temporary Resident IDs & Lifestyle Access With the purchase of Temporary Resident IDs ($50 per guest, paid directly to The Villages), guests receive full access to: All recreation centers and 70+ pools. 45+ executive golf courses and championship golf courses. Pickleball, tennis, fitness, clubs, and community activities. Entertainment across all three town squares. This home’s location offers unparalleled walkability, a rare find in The Villages — giving you direct access to the best dining, recreation, and entertainment the community has to offer. 📅 Whether you’re looking for a seasonal retreat, an extended getaway, or a lifestyle escape in the heart of The Villages, Avenida de las Casas is the perfect place to call home. 🛺 Book your stay and enjoy Spanish Springs like a true Villager.

Mission Hills Home (Mission Hills)

The Villages, FL, US
3 Bedrooms 4 Guests
Sep 30 - Oct 5
$166 night

Mission Hills Home – A Prime Location Near Lake Sumter Landing! 🌟 Welcome to Mission Hills Home – The Perfect Villages Getaway! 🌟 Located in the highly desirable Mission Hills neighborhood, this beautiful 3-bedroom, 2-bathroom home offers the ultimate combination of convenience, comfort, and modern charm. With the Mission Hills Trail Pool & Recreation Area right across the street, you’ll have a pool, bocce, walking trails, and outdoor activities just steps away. Even better, Lake Sumter Landing is only minutes away! Walk or take the included 2-seater golf cart with comfortable bucket seats to explore live music every night, a scenic waterfront boardwalk, a variety of restaurants, boutique shops, and even a movie theater! The home’s prime location also provides easy access to some of The Villages’ top golf courses, shopping, and recreation centers. 🏡 Home Features & Comfort Spacious Master Suite: Features a king-size bed, ensuite bathroom, and a walk-in closet. Two Beautiful Guest Rooms: Both with very comfortable queen beds. Bright & Modern Design: Neutral tones make the home feel airy, inviting, and relaxing. Open-Concept Kitchen & Dining: Fully equipped kitchen with ample counter space, modern appliances, and a spacious dining area—perfect for entertaining. Comfortable Living Area: Features plush seating, including a recliner, ideal for relaxing after a day of fun. Private Fenced Backyard & Lanai: Enjoy a morning coffee or an evening meal on the fully furnished lanai. Laundry Room: Full-size washer and dryer for convenience. 2-Seater Golf Cart Included! Explore all The Villages has to offer with ease. 🌴 PRIME LOCATION – The Best of Lake Sumter Landing at Your Doorstep! Lake Sumter Landing is one of The Villages’ most vibrant and exciting destinations, offering: Live Music & Entertainment Every Night at Market Square. Amazing Restaurants like City Fire, Red Sauce, Lighthouse Point, RJ Gators, and Cody’s Original Roadhouse. The Old Mill Playhouse Movie Theater – catch the latest films just minutes away. Boutique Shops & Specialty Stores for unique finds. A Scenic Boardwalk Along the Water – perfect for a leisurely evening stroll. Grocery Stores & Essential Shopping (Publix) within a short golf cart ride. 🏌️ GOLF & RECREATION – A Golfer’s Dream Location! Mission Hills Home is close to some of the best golf courses in The Villages, including: 40+ Executive Golf Courses – FREE to play with a Villages Resident ID! 12 Championship Golf Courses with stunning fairways. Mission Hills Trail Pool & Recreation Area right across the street for swimming, bocce, and social activities. Over 300 Pickleball Courts, tennis courts, and multiple recreation centers for endless activities. More than 100 miles of golf cart paths for exploring The Villages in style! 🐶 Pet Policy & Temporary Resident IDs Pet-Friendly (Upon Approval): Dogs only (no cats). Please send details about your dog before booking. The Villages Temporary Resident ID ($50 per couple) grants access to all pools, golf courses, and recreational facilities. ✨ Experience The Best of The Villages at Mission Hills Home! With its prime location, modern comforts, and access to incredible amenities, Mission Hills Home is the ideal retreat for those looking to experience the very best of The Villages. 📅 Book your stay today and make unforgettable memories in The Villages!

Magnolia Leesville Home

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 22 - 27
$95 night

🌸 Welcome to The Magnolia Blossom Home: Your Perfect Getaway in the Villages of Caroline! Situated just 8 minutes from Lake Sumter Landing, The Magnolia Blossom Home offers unparalleled comfort and convenience in the heart of the vibrant Villages of Caroline community. With a four-month minimum stay, you’ll have plenty of time to immerse yourself in all that this beautiful area has to offer. ✨ Impeccable Comfort & Convenience Step into a world of comfort and modern living with our open floor plan. This fully furnished three-bedroom, two-bathroom house is designed to provide an amazing experience for our guests. The master bedroom features a king-sized bed, while the second bedroom offers two twin beds, and the third bedroom includes a comfortable sofa bed. Enjoy the well-equipped kitchen and cozy living spaces that make The Magnolia Blossom Home the perfect vacation retreat. The enclosed lanai provides a serene spot for relaxation, whether with your morning coffee or an evening cocktail under the shade of the magnolia tree. 🏡 Community Charm & Neighborly Vibes Experience the warmth of community living in a neighborhood filled with friendly faces and welcoming smiles. Whether it’s a friendly chat with neighbors or a leisurely stroll around the beautifully landscaped grounds, you’ll feel right at home in this charming community. 🏊‍♂️ Recreation & Relaxation Indulge in endless opportunities for recreation and relaxation just minutes from your doorstep. Enjoy a refreshing retreat at the nearby pool and take advantage of the close proximity to Lake Sumter Landing and various recreational centers. The Villages offer ample opportunities for leisure, fun, and social activities, ensuring a vibrant lifestyle for all. 🚗 Location & Convenience The Magnolia Blossom Home emphasizes location and greenery, featuring a garage for one car and a two-seater golf cart, perfect for exploring the neighborhood and nearby attractions. Pets are welcome upon approval. No smoking or vaping. Your cozy home at The Magnolia Blossom Home in the Villages of Caroline awaits—come experience the ultimate blend of comfort, convenience, and community living!

The Villages Home 2 Mi to Farmers & Crafts Market

Lady Lake, FL, US
2 Bedrooms 4 Guests
Aug 20 - 27
$144 night

Community Pool | In-Unit Laundry | Golf Cart Provided | 1 Mi to Spanish Springs Square Nestled in the heart of Lady Lake, with easy access to shopping, dining, and entertainment, this 2-bedroom, 2-bath vacation rental is the perfect home base for a comfortable extended stay! Sip your morning coffee on the screened porch before exploring Spanish Springs Square or Lake Griffin State Park. As evening falls, whip up your favorite snacks in the kitchen and settle in for a laid-back movie night! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed COMMUNITY AMENITIES (visitor pass required) - Outdoor pool (heated), hot tub - Shuffleboard, bocce ball, pickleball - Access to The Villages golf courses (w/ fee) OUTDOOR LIVING - Furnished screened porch - Private patio INDOOR LIVING - 2 Smart TVs - Dining table, high-top seating KITCHEN - Refrigerator, dishwasher, stove/oven, microwave - Cooking basics, dishware & flatware - Drip coffee maker, coffee provided GENERAL - Free WiFi - Central A/C & heating - Washer & dryer - Linens/towels FAQ - Golf cart (waiver may be required) ACCESSIBILITY - Single-story home, small step for entry PARKING - Garage (1 vehicle) - Driveway (1 vehicle) -- THE LOCATION -- - Centrally located near shops, eats & nightly live music - 4 miles to Lake Sumter Landing - 6 miles to The Villages Polo Club - 8 miles to Lake Griffin State Park - 13 miles to Brownwood Paddock Square - 63 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 30 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story property requires a small step for entry - Guests must obtain a visitor pass to access the community pool and hot tub. Please reach out to the Guest Contact for more information - A waiver may be required prior to using the golf cart

Hernandez Hacienda at De La Mesa

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 20 - 24
$89 night

🌟 Hernandez Hacienda at De La Mesa 🌟 NEXT DOOR TO THE COMMUNITY POOL!!!! Welcome to Hernandez Hacienda at De La Mesa, a spacious 3-bedroom, 2-bathroom retreat with an additional office space and plenty of extras to make your stay in The Villages unforgettable. Perfectly located right next to the De La Mesa community pool and park, this home combines comfort, convenience, and access to everything The Villages lifestyle has to offer. 🏡 Home Features Bedrooms & Bathrooms: Master suite with King bed Two guest bedrooms with Queen beds Murphy bed (Full) located in the common area for flexible sleeping options Two full bathrooms for guest convenience Office Space: Dedicated workspace for two, ideal for remote work or personal projects. Living & Dining: Large seating areas with comfortable furnishings, designed for relaxation or entertaining. Kitchen: Fully equipped with everything you need to prepare meals at home. Outdoor Living: A huge patio space perfect for dining al fresco, entertaining, or enjoying Florida’s sunshine. Garage & Cart: Includes a 2-seater golf cart available for guest use (with signed liability waiver release). 📍 Location Highlights Community Pool & Park: Just steps away — directly next to the home. Spanish Springs Town Square: Only minutes away, offering nightly live music, dining, and shopping. Lake Sumter Landing: A short ride for waterfront dining, entertainment, and festivals. Golf: Quick access to both executive and championship golf courses nearby. Recreation Centers: Close to multiple centers offering pickleball, tennis, bocce, shuffleboard, fitness rooms, and social clubs. 🌿 Explore The Villages Lifestyle With a Temporary Resident ID ($50 fee paid to The Villages), you’ll enjoy access to: 40+ executive golf courses and numerous championship courses Dozens of adult and family pools Recreation centers with fitness, arts, games, and clubs Over 3,000 clubs and activities Nightly live music at the three town squares: Spanish Springs, Lake Sumter Landing, and Brownwood Paddock Square Scenic walking, biking, and golf cart trails connect you to shops, restaurants, and entertainment across the community. 🐾 Pet & Guest Policies Dogs welcome upon approval No cats No smoking or vaping anywhere on the property 👉 Hernandez Hacienda at De La Mesa offers the perfect mix of comfort, convenience, and lifestyle. Whether you’re relaxing by the pool next door, golfing across The Villages, or heading to Spanish Springs for a night of music, this home puts you in the heart of it all.

Gardenia Bancroft Home (Virginia Trace)

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 31 - Sep 5
$124 night

🌟 Gardenia Retreat Home in Virginia Trace, The Villages, FL 🌟 Experience the perfect blend of luxury and location with this beautifully upgraded 3-bedroom, 2-bathroom home nestled on a quiet cul-de-sac in the desirable Village of Virginia Trace. Just a short walk (8 minutes) to LAKE SUMTER LANDING, this home offers a prime location paired with exquisite features and thoughtful design. Less than a mile to Mallory Country Club championship golf and dining. Just over a mile to two executive golf courses. Neighborhood pool just over a block and Canal St. Recreation Center half a mile. 🏡 Elegant Living Spaces & Thoughtful Upgrades Step inside to find a home that exudes elegance and comfort. Double crown molding throughout adds a touch of sophistication, while solar tubes provide additional natural light, creating a bright and airy atmosphere. The spacious master suite boasts two closets, double vanities, and a luxurious Roman shower, offering a private retreat within your home. Pocket doors separate two guest bedrooms and a bath, ensuring privacy for your visitors. Sleeps six comfortably. Two 55-inch Samsung Smart TV with DVR’s so you can record your favorite shows. 🍳 Gourmet Kitchen for the Home Chef The heart of this home is the stunning gourmet kitchen, perfect for the home chef. It features a gas double black stainless convection oven and microwave, stacked kitchen cabinets with glass, and granite countertops throughout. An informal dining or sitting area and a tiled breakfast bar make this space as functional as it is beautiful, ideal for both everyday meals and entertaining guests. BBQ grill included. Screened in lanai so you can enjoy your meals in the outside air. 🌳 Outdoor Living & Mature Landscaping Enjoy Florida’s beautiful weather from the comfort of your screened lanai with stone flooring, surrounded by mature landscaping that offers both beauty and privacy. The paver driveway and walkway add to the curb appeal, making a great first impression for you and your guests. 🚶 Prime Location & Amenities Located just off Canal Street and near the VIRGINIA TRACE POOL and CANAL STREET RECREATION CENTER, this home offers convenient access to everything The Villages has to offer. A short walk will take you to Lake Sumter Landing, where you can enjoy shopping, dining, and entertainment in a vibrant community setting. 🎟️ Exclusive Villages Amenities With a Villages Temporary Resident ID (available for a $50 fee paid directly to The Villages), you’ll gain access to 40+ executive golf courses, offering a variety of challenges for all skill levels. These courses are included in the amenities accessible during your stay, making it easy to enjoy a round of golf in the beautiful Florida sunshine. Each town square features LIVE MUSIC EVERY DAY, along with numerous events and festivals, creating a lively and engaging atmosphere. 🛏️ Comfortable Bedroom Layout Bedroom 1: One King Bedroom (sleeps 2 guests) Bedroom 2: One Queen Bedroom (sleeps 2 guests) Bedroom 3: Two Twin Beds (sleeps 2 guests) This home comfortably sleeps 6 guests, making it perfect for families or groups looking to enjoy all that The Villages has to offer. 🌴 Embrace The Villages Lifestyle This upgraded Gardenia Retreat Home offers more than just a place to stay; it provides an opportunity to live the vibrant and luxurious lifestyle that The Villages is known for. From its prime location near Lake Sumter Landing to its elegant features and access to world-class amenities, this home is the ideal retreat for your next Florida getaway. Don’t miss your chance to experience the best of The Villages in this stunning Virginia Trace home!

Peaceful Lady Lake Home w/ Screened-In Porch!

Lady Lake, FL, US
2 Bedrooms 4 Guests
Oct 11 - 13
$132 night

Let this newly renovated 2-bedroom, 2-bath vacation rental set the scene for your next getaway! Enjoy a cup of coffee in the sunroom, pick a fresh lemon or an orange from the trees, then take a golf cart around to the many community amenities. Located less than a mile from Spanish Springs Town Square, this home invites you to spend time shopping, dining, and enjoying live music. Take a day trip to Silver Springs State Park to walk the trails throughout the largest artesian spring in the world! -- THE PROPERTY -- Free WiFi | Remote-Work Friendly | 1,600 Sq Ft | Resort-Style Amenities Whether you’re seeking to explore each corner of Florida or need some time away for a peaceful coastal retreat, this serene home offers well-appointed amenities and a prime location near the ocean! Bedroom 1: Queen Bed | Bedroom 2: Queen Bed VILLAGES FLORIDA AMENITIES (available w/ passes): Golf cart access, 3 community pools, clubhouse, basketball court, golf course, playground, tennis court, rec center, pickleball, bocce ball, shuffleboard LADY LAKE LIVING: Smart TVs, ceiling fans, beach towels, patio, outdoor dining/seating areas, screened-in porch KITCHEN: Fully equipped, stainless steel appliances, Keurig coffee maker, Crock-Pot, microwave, toaster, blender, ice maker, water filter, dishware/flatware, spices, basic cooking essentials GENERAL: Central A/C & heating, washer/dryer, laundry detergent, iron/ironing board, towels/linens, hair dryers, complimentary toiletries, trash bags/paper towels FAQ: Step-free access, community pass fees required for amenities (paid on-site) PARKING: Garage (2 vehicles), driveway (4 vehicles), free street parking -- THE LOCATION -- OUTDOOR RECREATION: Lake Miona Park (5.7 miles), Lake Griffin State Park (7.7 miles), Lake Weir (8.1 miles), Lake Okahumpka Park (10.1 miles), Carney Island Recreation & Conservation Area (12.2 miles), Silver Springs State Park (22.1 miles), Dade Battlefield Historic State Park (28.5 miles) ATTRACTIONS: Spanish Springs Town Square (0.7 miles), Uncle Donald’s Farm (3.2 miles), Lake Sumter Landing Market Square (4.5 miles), Grand Oaks Resort (4.5 miles), Brownwood Paddock Square -free concert series (9.5 miles), Paquette’s Historical Farmall Museum (12.4 miles), GatorWorld Parks of Florida (14.0 miles), Disney World (58.0 miles) TEE TIME: Truman Executive Golf Course (6.1 miles), Sarasota Golf Practice Center (6.3 miles), Bonifay Golf & Country Club (7.2 miles), Evans Prarie Golf and Country Club (7.5 miles), Belle Glade Golf & Country Club (7.7 miles), Southern Oaks Golf (12.2 miles) AIRPORTS: Orlando International Airport (63.8 miles), Tampa International Airport (90.9 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: Please be aware community passes are required to use the amenities. The cost is $50 for the first 2 people and $50 for each additional person - NOTE: Guests are able to use the pool and courts without a pass with their own equipment but will not be able to rent equipment without a pass. Please download The Villages app for additional information

Gardenia Bancroft Home (Virginia Trace)

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 30 - Sep 3
$102 night

WALKING DISTANCE TO LAKE SUMTER LANDING!! Experience the perfect blend of comfort, style, and location at Bancroft Retreat at Virginia Trace, a beautifully maintained 3-bedroom, 2-bathroom home nestled on a quiet roundabout in one of The Villages’ most desirable neighborhoods. Just minutes from Lake Sumter Landing, this inviting home places you close to championship golf, recreation centers, neighborhood pools, shopping, dining, and nightly live entertainment. Less than a mile from Mallory Hill Country Club with championship golf and dining, just over a mile from two executive golf courses, and only a short distance to the Virginia Trace Neighborhood Pool and Canal Street Recreation Center, you’ll enjoy easy access to everything The Villages has to offer. 🏡 Comfortable Living Designed for Relaxation Step inside and feel right at home in the spacious, open living area featuring comfortable reclining seating—perfect for relaxing after a day of golf, exploring the town squares, or enjoying Florida’s beautiful weather. One of the home’s standout features is the temperature-controlled enclosed lanai, offering comfortable year-round enjoyment with plenty of seating for morning coffee, afternoon reading, or evening gatherings with family and friends. The lanai is also accessible directly from the primary suite, creating a peaceful extension of your private retreat. The living room and primary bedroom each feature Smart TVs, making it easy to unwind with your favorite shows after a fun-filled day. 🍳 Fully Equipped Kitchen Whether you’re preparing a quick breakfast before heading out or cooking dinner at home, the fully equipped kitchen provides everything you need for a comfortable stay. The open layout makes entertaining and spending time together easy and enjoyable. 🛏️ Comfortable Bedroom Layout Primary Suite King Bed Smart TV Private access to the enclosed lanai Sleeps 2 Guest Bedroom 1 Queen Bed Sleeps 2 Guest Bedroom 2 Queen Bed Sleeps 2 This home comfortably accommodates up to six guests, making it perfect for couples, families, or friends traveling together. 🌴 Relax & Enjoy the Florida Lifestyle The enclosed climate-controlled lanai offers an inviting space to enjoy your morning coffee, share meals, play cards, or simply relax after a day of activities. Located on a peaceful roundabout, the home provides a quiet setting while remaining close to the many attractions and amenities that make The Villages such a popular destination. 📍 Prime Virginia Trace Location Conveniently located near Canal Street, you’ll be just minutes from: Lake Sumter Landing Town Square Virginia Trace Neighborhood Pool Canal Street Recreation Center Mallory Hill Country Club Executive Golf Courses Restaurants, shopping, grocery stores, and nightly live entertainment 🎟️ Enjoy The Villages Lifestyle Guests may purchase a Temporary Resident ID directly from The Villages for $50 per household. This optional pass provides access to many of The Villages’ outstanding recreational amenities, including: 40+ Executive Golf Courses (greens fees included; trail fees apply) Recreation Centers Adult and Family Swimming Pools Pickleball, Tennis, Bocce, and Shuffleboard Courts Hundreds of clubs, classes, and organized activities Nightly live entertainment at all three Town Squares The Temporary Resident ID is a wonderful way to experience the unique lifestyle that has made The Villages one of Florida’s premier active adult communities. 🐾 Pet Policy Dogs are welcome with prior approval. Cats are not permitted. 🌟 Your Perfect Florida Getaway Whether you’re planning an extended seasonal stay or a relaxing vacation, Bancroft Retreat at Virginia Trace offers the perfect combination of comfort, convenience, and location. Enjoy peaceful surroundings, exceptional amenities, and easy access to everything that makes The Villages one of Florida’s most sought-after destinations. We look forward to welcoming you to your home away from home!

The Jefferson Retreat (Amelia)

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 20 - 25
$89 night

Jefferson Retreat – A Romantic Escape in The Villages of Amelia 🌴 Tranquility, Style, and the Comfort of The Villages Lifestyle 🌴 Welcome to Jefferson Retreat, a thoughtfully designed and uniquely cozy 3-bedroom, 2-bathroom home located in the highly desirable Villages of Amelia. This charming home stands apart with its romantic ambiance, deep-toned finishes, and a more intimate feel—perfect for those who appreciate a warm, cocoon-like space that contrasts with the bright Florida sun. From the moment you step inside, you’ll feel a calming energy. Unlike the bright and breezy vacation homes found throughout The Villages, Jefferson Retreat embraces a moodier palette with elegant wall tones and a snug interior atmosphere that invites you to unwind. It’s a perfect space to curl up with a good book, enjoy a quiet evening indoors, or share a candlelit dinner with someone special. 🛏️ Comfortable and Private Accommodations Master Suite with a king-sized bed, walk-in closet, and ensuite bathroom with walk-in shower Two guest bedrooms, one with a king bed and the other with a queen bed. Guest bathroom includes a full tub/shower combo Fully equipped kitchen with kitchen island and bar seating Comfortable living room with reclining seating, perfect for movie nights or relaxing Laundry room with washer and dryer Enclosed lanai with outdoor seating to enjoy the peaceful surroundings 🐶 Pet Policy: One dog may be approved upon request. Please include breed, weight, and age when submitting your inquiry. We are happy to consider well-behaved furry friends! 🎾 Location, Location, Location – Explore The Best of The Villages of Amelia! Jefferson Retreat is ideally situated near many of The Villages’ most popular destinations: Lake Sumter Landing (Just 10 minutes away by golf cart) Enjoy live music every evening, waterfront dining, unique shops, and local events in this charming square inspired by Old Key West. Amelia Recreation Center (less than 5 minutes away) Pickleball, bocce, shuffleboard, adult pool, billiards, cards, and social events. Mallory Hill Country Club (3 minutes away) Dine in the clubhouse or golf at this 27-hole championship course. Havana Country Club (5 minutes) Another great dining and golfing option surrounded by scenic views. Bonifay and Cane Garden Country Clubs (under 15 minutes) More choices for championship golf and enjoyable meals. Odell and Bridgeport Recreation Centers (within 10 minutes) Indoor/outdoor recreation, walking paths, pools, and fitness options. 🚗 Explore The Villages by Golf Cart or Car The Villages is a vibrant 55+ community with over 100 recreation centers and pools, nightly entertainment at the town squares, and miles of golf cart paths connecting it all. A golf cart rental may be available—please inquire if you’re interested. 📌 Temporary Resident ID Information: Guests may purchase Temporary Resident IDs directly from The Villages for a $50 fee (per couple or single guest). This provides access to: All 40+ executive golf courses (free to play, just pay trail fees) Reduced rates at championship golf courses Full access to pools, recreation centers, and hundreds of clubs Activity registration, classes, and special events We’re happy to assist with the ID application process for a smooth experience. 🌟 Monthly & Seasonal Discounts Available Ask about special rates for monthly stays during off-season (May–October) and secure your preferred dates early. Jefferson Retreat is a hidden gem for those who appreciate a softer, more romantic aesthetic and a peaceful Villages lifestyle. We look forward to hosting you!

Medira Villa at Spanish Springs

Lady Lake, FL, US
2 Bedrooms 4 Guests
Aug 20 - 25
$83 night

Medira Villa at Spanish Springs Steps from Spanish Springs • Peaceful & Fully Equipped Villa • Fenced Yard • Walkability & the Full Villages Lifestyle Welcome to Medira Villa in Spanish Springs at Villages of Del Mar, a beautifully maintained 2-bedroom, 2-bathroom villa perfectly located just a 5-minute walk to Spanish Springs Town Square. This charming four-year-old home offers incredible walkability, privacy, and comfort—giving you the true Villages lifestyle from the moment you arrive. Whether you’re here to enjoy nightly entertainment, golf, recreation centers, or simply relax in a peaceful fenced yard, this villa has everything you need for a memorable stay. 🏡 PROPERTY FEATURES ✨ Interior Highlights Master Bedroom: King bed, smart TV for streaming, ensuite bathroom, spacious layout. Guest Bedroom: Queen bed, fully stocked with linens, pillows, and blankets. Two Full Bathrooms: Clean, bright, and equipped with all essentials. Fully Equipped Kitchen: Includes pots, pans, bakeware, utensils, dishes, glasses, cutting boards, coffee maker, toaster, and more—ideal for guests who love to cook. Cozy Living Area: Comfortable couches and a smart TV for relaxing at the end of the day. Fully Stocked: Linens, towels, and starter supplies are included for a seamless arrival. 🌿 OUTDOOR LIVING Fully fenced backyard offering privacy and tranquility. Large patio overlooking beautiful trees and green space. Ergolón lanai with morning-coffee seating. Outdoor dining table for 6, perfect for gatherings or al fresco meals. This peaceful outdoor space is one of the standout features of the home. 🐾 PET POLICY Dogs allowed upon approval Limit: 1 dog Cats are not permitted (Please disclose pet during booking request.) 📍 LOCATION — STEPS FROM SPANISH SPRINGS This villa is located right at the entrance of Spanish Springs, offering unmatched walkability. 🎶 Daily Entertainment (Every Night, 5–9 PM!) Spanish Springs hosts live music, dancing, and events every single night of the year. 🍽️ Restaurants & Bars Walk to some of the best dining in The Villages, including: Amerikanos McCall’s Tavern Ay! Jalisco TooJay’s Deli Margarita Republic …plus several cafés and grab-and-go options. 🛍️ Retail Shops Boutiques, salons, clothing stores, and specialty shops fill the square. 🍦 Treats & Sweets Kilwins Ice Cream & Chocolates Perfect for an evening stroll after music at the square. 🎥 Old Mill Playhouse Theater A charming local movie theater right in the heart of Spanish Springs. 💪 Spanish Springs Fitness Center Walkable gym access (guest passes available). And you are only a short drive or golf cart ride from Lake Sumter Landing, offering another waterfront square with dining, events, and nightly live music. 🏊 RECREATION CENTERS NEARBY You’ll have easy access to: La Hacienda Recreation Center Rio Grande Recreation Center Chula Vista Recreation Center Mira Mesa Executive Golf & Recreation Enjoy: Pools Pickleball courts Tennis Bocce Shuffleboard Billiards Indoor activities & social clubs 🏌️‍♂️ THE VILLAGES LIFESTYLE – TEMPORARY RESIDENT ID ($50) Guests may obtain Temporary Resident IDs for a $50 fee per household paid directly to The Villages. This pass provides access to: 40+ Executive Golf Courses (free to play; trail fees apply for carts) All Neighborhood & Family Pools All Recreation Centers Sports Courts: tennis, pickleball, bocce, shuffleboard & more Hundreds of Weekly Activities – fitness, crafts, clubs & workshops Full instructions will be provided after booking. 🚗 GOLF CART ACCESSIBLE This villa is located in a fully golf-cart-accessible area. If you’d like a golf cart during your stay, we will send trusted preferred rental vendors after booking. 🌳 HISTORIC SIDE OF THE VILLAGES – FULL EXPERIENCE Located in the charming Historic Section of The Villages, this area is loved for: Mature trees and landscaping Larger yard spaces Quaint residential streets Rich Villages heritage Close access to Hwy 441, retail, and medical centers This is where The Villages began—and where many visitors fall in love with the community. ⭐ SUMMARY Medira Villa at Spanish Springs offers: A premium walkable location Peaceful and fully equipped interior A private fenced yard Nightly entertainment minutes away Comfortable bedding and thoughtful amenities Full access to The Villages lifestyle You’ll enjoy comfort, convenience, and authentic Villages living from the moment you arrive.

Golf + Poolside Bliss! Retreat 2 Mi to Lake Sumter

Lady Lake, FL, US
3 Bedrooms 6 Guests
Oct 8 - 10
$120 night

Furnished Porch | Remote Work Friendly | Community Pickleball & Rec Centers | Disney Day Trips Dive into the vibrant Florida lifestyle! From lazy pool days to tee times on championship greens, you’ll find the ultimate launchpad at this vacation rental in The Villages. Enjoy the community perks or explore the premier shopping and dining at Lake Sumter Landing and Spanish Springs. Looking to wind down? Enjoy evening cocktails and conversation on the screened porch. Reserve your sunny escape! -- THE PROPERTY -- VILLAGE OF CAROLINE AMENITIES (addt’l $50 per person fee, paid on-site) - Outdoor pools (unheated) - Pickleball court - Recreation centers OUTDOOR LIVING - Furnished screened porch - Private backyard - Front patio w/ seating INDOOR LIVING - Open-concept layout - Office w/ dedicated workspace - Smart TV (bedroom 1) - Board games & books - 6-person dining area - Ceiling fans - Free WiFi KITCHEN - Refrigerator, dishwasher, stove/oven, microwave - Dishware & flatware, cooking basics - Keurig coffee maker ACCESSIBILITY - Single-story home, 1 step to enter PARKING - Garage (2 vehicles) - Driveway (2 vehicles) - Free street (first-come, first-served) - No RV parking -- THE LOCATION -- - Quiet residential area near golf, dining & Lake Sumter - 1 mile to Mallory Hill Country Club - 2 miles to Lake Sumter Landing - 3 miles to Cane Garden Country Club - 5 miles to Sharon L. Morse Performing Arts Center - 6 miles to Spanish Springs Town Square - 8 miles to Brownwood Paddock Square -- 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 - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 1 step to enter - The $50/person community amenities fee is paid to Lake Sumter Landing upon arrival. The pass is needed to use all amenities SECURITY CAMERA INFORMATION - 1 Ring exterior device - Location: front door - Coverage: front entry

Private Pool & Golf Cart! Villa By Spanish Springs

The Villages, FL, US
2 Bedrooms 6 Guests
Aug 21 - 26
night

Must Be 55+ to Book | Golf Cart Provided | Remote Work Ready This 2-bed, 2-bath vacation rental brings The Villages lifestyle right to your backyard! A private, solar-heated pool lets you swim through every season, the Florida room provides a sunny spot to work, and the courtyard patio is perfect for coffee or cocktails. Hop on the golf cart to discover everything from live music to local dining at Spanish Springs, then come home to a villa that feels like your own private retreat! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen Murphy bed - Living Room: 1 queen sleeper sofa THE VILLAGES AMENITIES (w/ $50 fee for 2 passes, paid on-site) - 100+ pools: family pools, indoor pools, sports pools & neighborhood pools - 107 unique recreation centers - 240+ pickleball courts, 201 bocce ball courts - 5 racquetball courts, 25 tennis courts - 174 shuffleboard courts - 930 acres of nature preserves w/ walking trails - Town squares w/ nightly live entertainment - 46 executive golf courses & 10 championship courses (prior reservations required) OUTDOOR OASIS - Private saltwater pool (solar-heated only) - Furnished patio, gas grill - Lounge chairs, umbrella - Landscaped garden HOME HIGHLIGHTS - 2 Smart TVs - Large dining table - Florida room, desk w/ printer - Washer & dryer KITCHEN - Refrigerator, stove/oven, dishwasher - Drip/Keurig coffee maker - Toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi - Central A/C & heating - Laundry detergent, iron & board - Linens & towels, shampoo, hair dryer FAQ - Golf cart & private pool (waiver required) - 55+ community ACCESSIBILITY - Single-story home, step-free access PARKING - Driveway (1 vehicle) - Free street parking (first-come, first-served)  -- THE LOCATION -- - Across the street from Tierra Del Sol Country Club: golfing, adults-only pool - 2 miles to Spanish Springs Town Square & Sharon L. Morse Performing Arts Center: dining, shops & events - 3 miles to Lake Sumter Landing: waterfront dining & boutique shopping - 9 miles to Brownwood Paddock Square & Barnstorm Theater - 13 miles to Sawgrass Grove & 15 miles to Eastport - 71 miles to Orlando Int'l 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 55 years old to book - Additional fees and taxes may apply - Photo ID will be required upon check-in ADDITIONAL INFORMATION - This single-story home offers step-free access - A waiver is required prior to using the golf cart and private pool - The pool is heated solely by rooftop solar panels, and the water temperature may vary and cannot be adjusted - This property is located in a 55+ active-adult community. The guest booking the property must be at least 55 years old - Guests may reach out to the Guest Contact to arrange the purchase of an amenities pass for $50. This fee includes 2 passes and a gate pass; extra passes may be purchased for an additional fee Licence number: DWE7000758

2 Mi to Lake Sumter Landing: Home in The Villages

The Villages, FL, US
3 Bedrooms 6 Guests
Oct 21 - 23
$132 night

The Village of Amelia | Quiet Neighborhood | Dog Friendly w/ Fee Enjoy easy access to world-class golf courses and vibrant town squares when you stay at this central vacation rental. Situated in the heart of The Villages, this home offers an inviting interior, a breezy lanai, and a golf cart — perfect for cruises to Lake Sumter Landing for nightly live music and waterfront dining! Whether you're teeing off or exploring local hotspots, this gem puts you in the center of the action. Book now! -- THE PROPERTY -- COMMUNITY AMENITIES (w/ addt'l fee, paid on-site) - Outdoor pool - Tennis courts, pickleball courts - Volleyball & shuffleboard courts - Rec center OUTDOOR LIVING - Screened lanai w/ dining area - Patio, gas grill (starter propane provided) - Screened front porch w/ seating - Golf cart - Gated community INDOOR LIVING - Smart TVs - Dining table, breakfast bar - Dedicated workspace - Open floor plan - Washer & dryer KITCHEN - Fridge, stove/oven, dishwasher, microwave - Keurig coffee maker (starter pods provided) - Toaster, blender, ice maker - Cooking basics, dishware/flatware ACCESSIBILITY - Step-free access, single-story home PARKING - Garage (1 vehicle) - Driveway (2 vehicles) -- THE LOCATION -- - Peaceful setting in The Village of Amelia community - Close to restaurants, golf courses & lakefront activities - The Villages Entertainment located at all nearby town squares (9:00 AM-5:00 PM daily) - 2 miles to Lake Sumter Landing: waterfront shops & eateries, live entertainment, boat tours - 6 miles to Lake Griffin State Park - 7 miles to Brownwood Paddock Square & Spanish Springs Town Square -- 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/ $50 fee (+ fees & taxes, dogs only) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story property offers step-free access - The Village of Amelia's community amenities are available with an additional fee of $50 per person; the fee can be paid on-site via cash or check - Golf cart available for an additional fee; please coordinate directly with the local Guest Contact.

Sunny Home w/ Golf Cart in The Villages!

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 31 - Sep 3
$242 night

Ensure a restful and stress-free getaway to the Sunshine State when you stay at this bright 3-bedroom, 2-bathroom vacation rental in The Villages. Kickstart your day with a coffee on the lanai before venturing out to explore the area's attractions! Shop, dine, and listen to live music at Sumter Landing, then head to a nearby golf course to practice your swing. Return home after a fun-filled day and whip up a family-favorite meal in the fully equipped kitchen before settling in for a movie night! -- THE PROPERTY -- Single-Story Home | Gated Community | Pool Access | Free WiFi Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Additional Sleeping: Pack ‘n Play THE VILLAGES COMMUNITY: Golf cart community w/ 50+ golf courses, live entertainment, pickle ball court, basketball court, fitness center, game room, outdoor pools HOME HIGHLIGHTS: Smart TV, dining table, en-suite bathroom, sunroom w/ gas fire pit, lanai w/ lounge chairs KITCHEN: Stainless steel appliances, stove/oven, microwave, refrigerator, dishwasher, dishware/flatware, breakfast bar GENERAL: Washer/dryer, linens/towels, complimentary toiletries, central air conditioning/heating, hair dryer, laundry detergent, iron/board FAQ: Step-free access, golf cart (waiver may be required) PARKING: Garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- THE GREAT OUTDOORS: The Villages Polo Club (2 miles), Sharon Rose Wiechens Preserve (8 miles), Eaton's Beach (11 miles), Carney Island Recreation & Conservation Area (14 miles), Ocala National Forest (21 miles) ATTRACTIONS: Lake Sumter Landing (3 miles), Savannah Center (3 miles), Marion County Museum of History and Archaeology (23 miles) DISNEY PARKS (~63 miles): Magic Kingdom Park, Disney's Animal Kingdom Theme Park, Epcot, Disney's Hollywood Studios, Disney Springs AIRPORT: Orlando International Airport (68 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 - Additional fees and taxes may apply - Photo ID may be required upon check-in

Lovely Lady Lake Home w/ Resort Amenities & Lanai!

Lady Lake, FL, US
2 Bedrooms 6 Guests
Aug 20 - Sep 3
$153 night

Stay in style at this 2-bedroom, 2-bath vacation rental in Lady Lakes, FL! Nestled in the Villages, this home offers direct access to upscale amenities like championship golf courses, luxurious pools, bocce courts, and more. When you’re not enjoying the perks, take advantage of the screened-in lanai, furnished patio, and 1 bicycle for cruising the paths all around the community. If you’re looking to venture out, take a short golf cart ride to Spanish Springs Town Square for your shopping needs! -- THE PROPERTY -- Golf Course Location | 55+ Retirement Community | Gas Grill Bedroom 1: King Bed | Bedroom 2: Queen Bed | Living Room: Sleeper Sofa COMMUNITY AMENITIES: 3 pools, recreation center, numerous organized activities, sports courts, golf courses (addt’l fee, paid on-site) MAIN FEATURES: 2 Smart TVs, sunroom, screened-in porch w/ lanai, outdoor dining area, adult bicycle KITCHEN: Microwave, stove/oven, refrigerator, dishwasher, dishware & flatware, coffee maker, ice maker, toaster, water filter GENERAL: Free WiFi (high speed), central A/C & heating, towels/linens, in-unit washer/dryer, hair dryer, iron/board, complimentary toiletries FAQ: Steps required to enter (single-story home), no cable PARKING: Carport (1 vehicle), driveway (1 vehicle) -- THE LOCATION -- LOCAL SHOPPING: Spanish Springs Town Square (2 miles), Lake Sumter Landing Market Square (5 miles), Brownwood Paddock Square (11 miles) OPT OUTSIDE: Eaton’s Beach (6 miles), Lake Griffin State Park (8 miles), Lake Weir (8 miles), Hampton Beach (10 miles), Lake Okahumpka Park (12 miles), Silver Springs State Park (22 miles) DISNEY WORLD (~59 miles): Walt Disney World Resort, Hollywood Studios, Animal Kingdom, Epcot, Magic Kingdom, Typhoon Lagoon Water Park, Disney Springs AIRPORT: Orlando International Airport (66 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: The property requires steps to enter - NOTE: This property is located in a 55+ retirement community and may not be suitable for children - NOTE: While the property does not have cable, it does offer Smart TVs and high-speed WiFi

Sunny Willow Villa Getaway

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 20 - 25
$95 night

🌴 Welcome to Sunny Willow Villa — The Villages, Florida 🌴 Escape to Sunny Willow Villa, a beautifully appointed 2-bedroom, 2-bath courtyard villa in the highly desirable Village of Tierra del Sol. Ideally situated in one of the most established and convenient areas of The Villages, this inviting home puts golf, recreation, shopping, dining, live entertainment, and everyday conveniences close at hand. Whether you’re spending the season in Florida, exploring The Villages lifestyle, visiting friends and family, or simply looking for a relaxing getaway, Sunny Willow offers the perfect combination of comfort, privacy, and location. 🏡 Your Private Courtyard Retreat One of the highlights of Sunny Willow is its private fenced courtyard, giving you your own peaceful outdoor space to enjoy Florida’s beautiful weather. Start the morning outside with coffee, relax with a book in the afternoon, or unwind beneath the evening sky after a day of golf and exploring The Villages. Inside, the villa is tastefully decorated and designed to feel welcoming and comfortable from the moment you arrive. With two bedrooms and two full bathrooms, the home provides plenty of space to settle in and enjoy an extended stay. 🐾 Traveling With Your Dog? Dogs may be welcomed with prior approval. We understand that your dog can be an important part of the family, and the courtyard-villa layout makes Sunny Willow especially convenient for guests traveling with a canine companion. All dogs must be disclosed and approved before booking. Additional pet requirements and/or a pet fee may apply. Please contact us with information about your dog before reserving so we can confirm approval. ⛳ A Fantastic Tierra del Sol Location Sunny Willow is located in the Village of Tierra del Sol, one of The Villages’ beautifully established communities. Golf lovers will appreciate being close to the Tierra del Sol Championship Golf Course, while the nearby Tierra del Sol Recreation Center offers additional ways to enjoy the Florida lifestyle. Tierra del Sol Recreation includes: • Adult swimming pool • Tennis • Bocce • Shuffleboard • Horseshoes • Gathering rooms • Picnic pavilion • Recreational activities and events The area is also convenient to additional executive and championship golf courses throughout The Villages. Whether golf is your passion or simply one of the many activities you’d like to enjoy during your stay, you’ll have plenty of options nearby. 🎶 Minutes From Spanish Springs Town Square One of the greatest advantages of staying in this area is easy access to Spanish Springs Town Square, the original Town Square of The Villages. Spanish Springs combines distinctive Spanish-inspired architecture with dining, shopping, entertainment, and a lively atmosphere that makes it a favorite gathering place. Best of all, the Square features FREE live entertainment every night, so you can head over after dinner, grab a drink, listen to a band, or dance under the stars. 🍽️ Dining at Spanish Springs You’ll have plenty of restaurants to choose from, including favorites such as: • Amerikanos Grille • Ay! Jalisco • Bella Vita Italian Steakhouse • Coastal del Mar Seafood Grill • Flippers Pizzeria • McCall’s Tavern • Panera Bread • Ruby Tuesday • CFS Coffee • Kilwin’s Chocolate & Ice Cream Whether you’re looking for seafood, Mexican cuisine, Italian favorites, casual American dining, pizza, coffee, cocktails, or dessert, Spanish Springs makes an easy evening destination. 🛍️ Shopping & Entertainment at Spanish Springs There’s much more than dining at the Square. Spend the afternoon browsing shops including: • Chico’s • Talbots • Soma • Boutique and specialty retailers • The Villages Logo Store Then stay for the evening entertainment. Spanish Springs is also home to: 🎭 The Sharon L. Morse Performing Arts Center — offering concerts, theater, comedy, and other live performances. 🎳 Spanish Springs Lanes — perfect for an afternoon or evening of bowling. 🎶 Nightly outdoor entertainment — live music and dancing in the Town Square. Spanish Springs underwent a major revitalization and reopened in 2026 with refreshed gathering areas, lighting, signage, and improvements while retaining the character of The Villages’ original Town Square. 🛒 Everyday Conveniences Close By Extended stays are easier when groceries, pharmacies, restaurants, and services are nearby. Spanish Plaines Shopping Plaza offers convenient access to everyday essentials, including: • Publix Super Market • Walgreens • The UPS Store • First Watch • Dunkin’ • Subway • Beauty and personal-care services • Banking and additional professional services Everything from stocking the refrigerator to picking up a prescription or grabbing breakfast can be handled nearby. 🌊 Explore Lake Sumter Landing Another favorite Villages destination within easy reach is Lake Sumter Landing Market Square. Designed around a picturesque lakefront setting, Lake Sumter Landing offers a completely different atmosphere from Spanish Springs. Stroll along the waterfront and boardwalk, browse the shops, enjoy dinner, and stay for free nightly live entertainment. Popular dining options include: • Chop House at Lake Sumter • City Fire • Cody’s Original Roadhouse • Lighthouse Point Bar & Grille • Redsauce • Thai Ruby • VKI Japanese Restaurant • Flying Biscuit Café • Panera Bread • Starbucks • Haagen-Dazs Lake Sumter Landing also offers numerous boutiques, shops, services, and waterfront gathering areas. It’s a wonderful destination for an afternoon stroll, dinner with friends, sunset by the water, or dancing in the Square. 🎾 So Much More Than Golf The Villages is famous for golf, but the recreation choices extend far beyond the fairways. Depending on guest eligibility and applicable Villages requirements, recreational opportunities throughout the community may include: 🏊 Swimming 🎾 Tennis 🏓 Pickleball ⛳ Championship & executive golf 🃏 Cards and social clubs 🎱 Billiards 🎳 Bowling 🚴 Biking 🚶 Walking paths 🎨 Arts, crafts and hobby groups 💃 Dancing and fitness activities 🎭 Live performances 🎶 Nightly entertainment With recreation centers, pools, courts, golf courses, clubs, activities, restaurants, and entertainment throughout the community, it’s easy to make every day different. 🚗 The Villages Lifestyle — Made for Exploring One of the joys of staying in The Villages is how easy it is to explore. Travel throughout the community by car or golf cart where permitted, heading out for breakfast, golf, shopping, recreation, dinner, or an evening of live music. From the established neighborhoods surrounding Tierra del Sol to Spanish Springs and the waterfront atmosphere of Lake Sumter Landing, Sunny Willow gives you an excellent home base for experiencing it all. 🌞 Stay Awhile at Sunny Willow Sunny Willow isn’t simply a place to sleep — it’s your opportunity to settle into the Florida lifestyle. Enjoy your morning coffee in the private courtyard. Spend the day on the golf course or at the pool. Meet friends for dinner. Browse the shops at Spanish Springs. Dance to live music beneath the Florida evening sky. Then return to the privacy and comfort of your own courtyard villa. For seasonal guests, extended stays, and anyone looking to experience the best of The Villages, Sunny Willow Villa is ready to welcome you. 🐾 Bringing a dog? Please contact us prior to booking for approval. We look forward to welcoming you to Sunny Willow Villa in beautiful Tierra del Sol! 🌴☀️

Allenwood Pool Home at The Villages

The Villages, Florida, US
3 Bedrooms 6 Guests
Aug 20 - 25
$174 night

Allenwood Pool House | Private Heated Pool • Outdoor Kitchen • Golf Cart • Near Lake Sumter Landing Escape to Allenwood Pool House, a beautifully appointed designer home in the desirable Village of Amelia, where resort-style outdoor living meets one of the most convenient central locations in The Villages. Featuring a private pool, outdoor kitchen, dedicated workspace, and complimentary golf cart, this home is perfect for golf vacations, extended stays, snowbirds, or simply enjoying everything The Villages has to offer. The Home This beautifully designed 3-bedroom, 2-bath home comfortably accommodates up to six guests with an open floor plan that creates the perfect gathering space for family and friends. Sleeping Arrangements Primary Suite: King bed, Smart TV, private ensuite bathroom with walk-in shower Guest Bedroom 1: Queen bed with Smart TV Guest Bedroom 2: King bed with Smart TV Guest bathroom with full bathtub Every bedroom includes its own television, and the spacious living room also features a large Smart TV for relaxing after a day exploring The Villages. Chef’s Kitchen Whether you’re preparing breakfast before golf or hosting dinner with friends, the kitchen is fully equipped with everything you’ll need. Features include: Granite countertops Large center island Gas stove Upgraded stainless steel appliances Fully stocked cookware, dishes, utensils, and small appliances Coffee maker Pantry storage Dining options include: Dining table seating for 6 Breakfast nook seating for 4 Kitchen island with bar seating Outdoor Living The backyard is designed to make every day feel like a vacation. Enjoy: Private swimming pool Optional pool heat (additional fee) Outdoor kitchen Covered lanai Comfortable outdoor seating Private patio terrace Whether you’re enjoying your morning coffee, grilling dinner, or relaxing by the pool after a round of golf, this outdoor space is one of the home’s highlights. Dedicated Workspace Need a quiet place to work? The den features: Desk Comfortable office chair Quiet space for remote work, reading, or conference calls Included Amenities Complimentary high-speed Wi-Fi Smart TVs in the living room and every bedroom Full-size washer and dryer Fully equipped kitchen Linens and towels provided Two-car garage Complimentary 2-passenger gas golf cart Explore The Villages The Village of Amelia is one of the most sought-after central neighborhoods in The Villages, offering easy golf cart access to shopping, recreation, golf, and entertainment. Lake Sumter Landing Approximately 4 miles | About 10–15 minutes by golf cart Lake Sumter Landing is one of The Villages’ three iconic town squares and features: Free nightly live entertainment Waterfront restaurants Boutique shopping Happy hours Coffee shops Ice cream Seasonal events Movie theater Brownwood Paddock Square Approximately 8 miles | About 20–25 minutes by golf cart or 15 minutes by car Brownwood offers: Free nightly live music Restaurants Shopping Farmers markets Seasonal festivals Dancing Entertainment throughout the year Recreation Nearby With Temporary Resident IDs, guests may enjoy access to The Villages’ outstanding recreation system, including neighborhood and regional recreation centers, pools, pickleball, tennis, bocce, shuffleboard, clubs, and organized activities. Amelia Neighborhood Recreation Center Approximately 2 minutes away Features include: Adult pool Shuffleboard Bocce Horseshoes Social activities Pavilion Colony Cottage Regional Recreation Center Approximately 10 minutes away Offers: Sports pool Pickleball Tennis Billiards Meeting rooms Daily activities Fitness classes Lake Miona Regional Recreation Center Approximately 10 minutes away Features: Sports pool Pickleball Tennis Fitness activities Arts & crafts Clubs Indoor recreation Golf Golf enthusiasts will love the location. Numerous Executive Golf Courses and Championship Golf Courses are just minutes away by golf cart, giving you endless opportunities to play throughout your stay. Shopping & Dining Within just a few minutes you’ll find: Publix Fresh Market Walmart Target Walgreens CVS Pharmacy Banking Medical facilities Countless restaurants Golf cart-accessible shopping and dining Temporary Resident IDs Guests staying with AJ Home Rentals may purchase Temporary Resident IDs (approximately $50 per household, payable directly to The Villages when picking up the IDs). Temporary Resident IDs allow eligible guests to enjoy many of the community’s outstanding amenities, including recreation centers, pools, executive golf (trail fees may apply), organized activities, and more. Please note that Temporary Resident IDs are not Guest Passes and are issued by The Villages based on eligibility and availability. Golf Cart A complimentary 2-passenger gas golf cart is provided for your convenience. Guests who wish to use the golf cart must complete AJ Home Rentals’ Golf Cart Waiver before arrival. The golf cart is provided as a complimentary amenity. While we make every effort to ensure it is available, unforeseen maintenance, repairs, recalls, weather, or other circumstances may occasionally prevent its use. No refunds or credits will be issued for golf cart interruptions. Pet Policy We welcome well-behaved dogs upon prior approval. Dogs require advance approval. Breed, age, weight, and house-training information may be requested. Additional pet fees may apply. Cats are not permitted. Whether you’re planning a golf getaway, an extended seasonal stay, or a relaxing Florida vacation, Allenwood Pool House offers the perfect blend of comfort, convenience, and resort-style living in the heart of The Villages. From the private pool and outdoor kitchen to the golf cart and unbeatable location near Lake Sumter Landing and Brownwood, everything is here for an unforgettable stay.

Whimsy Willow (Winifred)

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 22 - 27
$107 night

Welcome to Whimsy Willow Village of Winifred | The Villages, FL Tucked beneath the graceful arms of a magnificent backyard tree and professionally styled with your comfort in mind, Whimsy Willow offers a warm, inviting home base for your next Villages getaway. From coffee in the lanai to scenic golf cart rides, this beautifully decorated 2-bedroom home has everything you need for a peaceful, rejuvenating stay in Florida’s premier 55+ community. 🛏️ Home Features 2 Bedrooms / 2 Bathrooms Master Suite: King-sized bed, premium linens, ample closet space Guest Bedroom: Queen-sized bed with soft textures and natural lighting Spacious Living Area with plush recliner and comfortable seating Fully Equipped Kitchen: All essential cookware, coffee maker, and modern appliances for easy meals at home Bright & Airy Lanai: Enjoy your morning brew or a glass of wine in a serene space with a view of the majestic backyard tree—a guest favorite! 🛺 Included Amenities 2-Seater Golf Cart: Cruise the community in style—explore pools, restaurants, and entertainment at your leisure High-Speed Wi-Fi & Smart TVs: Stay connected and stream your favorites Washer/Dryer: In-unit laundry for your convenience Driveway Parking 🧭 Location – Village of Winifred Situated in a prime central location, the Village of Winifred places you close to everything The Villages is known for. Enjoy easy access by golf cart or car to world-class recreation, golf, shopping, and entertainment. 🎾 Closest Recreation & Amenities: Winifred Neighborhood Pool – a short golf cart ride for a relaxing swim Seabreeze Regional Recreation Center – full gym, billiards, cards, arts & crafts, and more Lake Miona Regional Recreation Center – large sports courts, family pool, fitness trails ⛳ Closest Golf Courses: Bonita Pass Executive Golf Course Briarwood Executive Course Glenview Champions Golf & Country Club (Championship, fee applies) 🎉 Entertainment & Town Squares Just a quick ride away, enjoy the best of The Villages’ lifestyle with three lively town squares nearby: Lake Sumter Landing – waterfront charm, live music every night, dining, movies, and boutiques Spanish Springs Town Square – old-world architecture, festivals, and unique shops Brownwood Paddock Square – Western-themed entertainment, weekly farmer’s markets, and local eats 🛍️ Nearby Shopping & Essentials Publix, Walmart Neighborhood Market, and pharmacies within a short drive Golf cart accessible retail plazas with salons, banking, and dining 🏡 Community Details Located in The Villages – a 55+ community (at least one guest must be 55+) No Pets Allowed – we maintain an allergy-friendly environment No Smoking or Vaping on Premises 🎟️ Temporary Resident ID – Full Access For a one-time $50 fee paid directly to The Villages, guests can obtain a Temporary Resident ID, which provides: Access to 40+ Executive Golf Courses (free to play, $4 trail fee applies) Access to Championship Courses (additional fee) Entry to 70+ Pools and 100s of Recreation Centers & Clubs Participation in hundreds of social clubs, activities, and sports, including pickleball, tennis, bocce, shuffleboard, archery, arts & crafts, woodworking, and more! 🌞 Why You’ll Love Whimsy Willow Thoughtfully decorated with comfort and style in mind Beautifully shaded backyard with Florida charm Perfectly located to enjoy all that The Villages offers—whether you’re here for golf, recreation, social connection, or just pure relaxation Ready to unwind under the willow and embrace the good life? We can’t wait to welcome you to Whimsy Willow.

Rhapsody Retreat in The Villages

The Villages, FL, US
3 Bedrooms 5 Guests
Aug 20 - 25
$108 night

Rhapsody Retreat in The Villages | Hadley 3BR w/ Bikes, Office & Dual Lanais Welcome to Rhapsody Retreat, your beautifully appointed home-away-from-home in the highly desirable Village of Hadley in The Villages, Florida. Ideally located between Lake Sumter Landing and Brownwood Paddock Square, this inviting 3-bedroom, 2-bath home offers the perfect balance of comfort, convenience, and classic Villages living. Whether you’re visiting for a month of sunshine, a seasonal escape, a home search trip, or an extended stay to experience The Villages lifestyle, this home is thoughtfully prepared to help you settle in and enjoy every day with ease. Comfortable, Open Living Designed for Relaxation Step inside and enjoy a bright, welcoming floorplan with comfortable furnishings and all the essentials for an easy stay. The living area is designed for relaxing after a day of golf, recreation, shopping, or live entertainment — featuring comfortable recliners, a TV in the main living area, and a cozy setup that makes it easy to feel right at home. This home offers a practical and inviting layout for couples, seasonal guests, friends traveling together, or anyone wanting a peaceful and well-located Villages retreat. Sleeping Arrangements This home comfortably accommodates guests with a flexible and functional layout: Primary Bedroom: King bed, TV, comfortable furnishings, and private ensuite bath Guest Bedroom #1: Queen bed, TV, and cozy setup for visiting family or friends Guest Bedroom #2 / Flex Room: Office setup plus a full futon, making it a great space for remote work, reading, or additional sleeping arrangements This extra-flexible bedroom arrangement makes the home especially attractive for longer stays. Fully Equipped Kitchen The kitchen is fully stocked and ready for everyday living — whether you’re preparing breakfast before heading out for the day, making lunch between activities, or enjoying a relaxed dinner at home. You’ll enjoy a fully equipped kitchen with everything needed for: Cooking and meal prep Coffee and morning routines Dining in comfortably during longer stays Hosting a casual dinner or easy evening meal This is a home where it’s easy to unpack, settle in, and live comfortably. Indoor + Outdoor Florida Living One of the best features of this home is the ability to enjoy both indoor comfort and outdoor Florida living. Enclosed Lanai The enclosed lanai offers a wonderful bonus sitting space where you can enjoy your morning coffee, relax with a book, or simply unwind in comfort throughout the day. Outdoor Lanai / Patio Seating Area The home also offers a nice outdoor seating area, perfect for: Playing cards Enjoying dinner outside Relaxing after a day on the town Sharing a drink in the evening Florida air It’s a lovely extension of the home and a wonderful place to enjoy the Villages lifestyle. Extras That Make Your Stay Easy This home includes several thoughtful extras to help make your stay more enjoyable: 2 adult bicycles Comfortable recliners in the living area TV in the living room TV in the primary bedroom TV in the guest bedroom Fully equipped kitchen Office / flex room setup Comfortable outdoor spaces Location: Village of Hadley The Village of Hadley is one of the most desirable and well-positioned areas in The Villages because of its central location and easy access to some of the community’s most popular destinations. One of the biggest advantages of staying here is that you are located between Lake Sumter Landing and Brownwood Paddock Square, making it easy to enjoy two of the most loved town squares in The Villages. This means you can enjoy a wide variety of dining, shopping, golf cart rides, entertainment, and recreation without feeling tucked too far in one direction. It is a fantastic location for guests who want to experience a little bit of everything. Close to Lake Sumter Landing A stay here places you within easy reach of Lake Sumter Landing Market Square, one of the most iconic and charming destinations in The Villages. At Lake Sumter Landing, you’ll enjoy: Waterfront-style square atmosphere Great restaurants and casual dining Boutique shopping Outdoor entertainment and nightly live music Movie theater nearby Scenic walking areas and gathering spaces A lively but relaxed Villages atmosphere Lake Sumter is a favorite for guests who love to spend an afternoon or evening dining, walking the square, enjoying music, and soaking in the social energy of The Villages. Also Convenient to Brownwood Paddock Square You’re also well-positioned to enjoy Brownwood Paddock Square, another favorite destination in The Villages known for its warm western-style charm and lively evening atmosphere. At Brownwood, guests love: Nightly live music and entertainment Great dining options Wine bars and casual evening spots Shopping and boutiques Seasonal events and community gatherings A fun, energetic Villages social scene Being able to easily enjoy both Lake Sumter Landing and Brownwood is one of the biggest lifestyle advantages of this home. Easy Access to Shopping, Dining & Daily Convenience This area also offers easy access to many of the practical conveniences guests appreciate during longer stays, including: Grocery stores Restaurants Pharmacies Banking Everyday shopping Medical and service conveniences This makes it easy to enjoy your stay whether you plan to stay active every day or simply settle in and live comfortably for a while. Recreation Centers, Pools & Activities One of the best parts of staying in The Villages is the incredible lifestyle and amenities available throughout the community. Guests staying here can enjoy convenient access to many of the activities that make The Villages so special, including: Recreation centers Adult pools Family pools Pickleball Tennis Bocce Shuffleboard Walking and biking paths Fitness classes Arts & crafts Clubs and social groups Executive golf courses Championship golf nearby Town square entertainment Seasonal and community events Whether you want to stay busy every day or simply enjoy a few favorite activities during your stay, this location makes it easy to do both. The Villages Lifestyle Guest IDs Guests may have the option to obtain temporary Villages Guest IDs, which can provide access to many of the community amenities and help you enjoy more of the Villages lifestyle during your stay. Guest IDs may include access to many recreational amenities and community features, subject to current Villages policies and availability. Please note: Some amenities, executive golf tee times, and recreational access may be subject to guest rules, fees, and availability depending on the season and current Villages guidelines. We are always happy to help guide guests on what to expect before arrival. Pet Policy Dog considered upon owner approval. We know many guests love to travel with their furry companion, and we may be able to accommodate one dog upon approval. Please inquire in advance with: Breed Weight Age Whether the pet is fully house trained Pet approval is not automatic and must be cleared before booking. Why Guests Love This Home This home is a wonderful fit for guests looking for: A 3-bedroom, 2-bath layout A central Villages location Easy access to Lake Sumter Landing and Brownwood A fully equipped kitchen A comfortable enclosed lanai A nice outdoor seating space 2 bikes for enjoying the area A home that feels welcoming, practical, and easy to enjoy Whether your perfect day includes morning coffee on the lanai, an afternoon bike ride, golf, shopping, dinner on the square, or live music at night, Rhapsody Retreat offers a wonderful place to come home to.

Fieldbrook Cozy Designer Home (Pinellas)

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 29 - Sep 3
$124 night

IMPORTANT !!! JAN & FEB require to be booked together / no partial bookings allowed Experience the charm of The Villages, FL, in this beautifully furnished 3-bedroom, 2-bath home nestled in the highly sought-after Villages of Pinellas. 🌿 With a serene view of lush greenery and landscaping, this home offers a peaceful retreat while being close to all the action. Featuring a spacious lanai perfect for hosting gatherings or enjoying quiet evenings outdoors, the home is designed for comfort and relaxation. Inside, the open floor plan includes a cozy nook with ample seating, making it ideal for entertaining or enjoying family time. The master suite boasts a luxurious king bed, while the guest bedroom offers a queen bed, and the third bedroom has two twin beds for added versatility. 🛏️👑 Convenience is key with a two-car garage and a roomy driveway for plenty of parking. 🚗 Whether you’re an avid golfer or a shopping enthusiast, the Villages of Pinellas is known for its proximity to pristine golf courses, retail spots, and all the fantastic amenities The Villages has to offer. Plus, you’re just minutes away from the lively entertainment, dining, and events at Brownwood Paddock Square! 🎶🍽️ Golf & Amenities Living in The Villages means having access to world-class golf courses, from executive to championship-level options. Whether you’re a seasoned player or just starting out, you’ll enjoy an array of courses right at your fingertips, including those surrounding the Pinellas area. ⛳ The Villages is truly a golfer’s paradise! Beyond golf, the community offers an abundance of recreational activities. Enjoy arts and crafts, tennis, pickleball, bocce ball, swimming, outdoor fitness, and much more. With top-notch amenities and recreation centers, staying active and engaged is easy. 🎨🎾🏊‍♂️ Explore The Villages Step into a vibrant lifestyle filled with endless entertainment and opportunities to connect with neighbors. The Villages boasts year-round live music, with 365 days of events in the squares. From live bands to festivals, there’s always something happening. The Villages also offers a thriving arts scene, with classes, performances, and exhibits. 🎉🎶 Explore nature trails, enjoy outdoor fitness areas, and indulge in delicious dining at popular spots like Brownwood Paddock Square. Whether you’re looking for a quiet escape or an active social scene, The Villages offers the best of both worlds. Bedroom Layout: Master Bedroom: 1 King Bed (2 guests) Guest Bedroom: 1 Queen Bed (2 guests) Third Bedroom: 2 Twin Beds (2 guests) This meticulously clean and fully equipped home offers the perfect balance of luxury and convenience. Don’t miss your chance to live in one of Florida’s premier 55+ communities. 🌞 Contact us today to make this Pinellas Retreat your new home! 🏡🌴

The Wotring Retreat | Heart of The Villages

The Villages, FL, US
3 Bedrooms 5 Guests
Aug 20 - 25
$102 night

Wotring Retreat | Designer 3BR Retreat • Fenced Backyard • Forward-Facing Golf Cart • Near Brownwood & Lake Sumter Landing Escape to Wotring Retreat, a beautifully updated designer home nestled in the desirable Village of Pine Ridge in The Villages®, Florida. Whether you’re planning a month-long winter getaway, a golf vacation with friends, or simply looking to experience one of Florida’s most unique communities, Wotring Retreat offers everything you need to relax, recharge, and enjoy the famous Villages lifestyle. Beautifully furnished, thoughtfully equipped, and ideally located, this inviting home offers easy golf cart access to championship golf, recreation centers, shopping, restaurants, nightly live entertainment, and miles of scenic golf cart paths. 🏡 Welcome Home This beautifully updated 3-bedroom, 2-bath designer home comfortably accommodates up to six guests and features an open-concept floor plan designed for both relaxation and entertaining. Large windows fill the home with natural light while the spacious living room invites you to unwind after a day exploring The Villages. Watch your favorite shows on the large Smart TV, enjoy a quiet evening with family and friends, or simply relax in the comfortable seating after a day on the golf course. The open layout flows seamlessly from the living room into the dining area and kitchen, creating the perfect gathering space for everyone. 🛏 Sleeping Arrangements Primary Suite King Bed Private ensuite bathroom with walk-in shower Smart TV Spacious walk-in closet Guest Bedroom Two Queen Bed Guest Bedroom Three Queen Bed A second full bathroom is conveniently located near both guest bedrooms. Quality linens, towels, pillows, and starter essentials are provided for your arrival. 🍳 Fully Equipped Kitchen Whether you’re preparing breakfast before an early tee time or enjoying dinner after an evening at Brownwood, you’ll find everything needed to cook and entertain with ease. The beautifully updated kitchen is fully stocked with quality cookware, dinnerware, glassware, utensils, and a variety of small appliances. You’ll also find everyday conveniences including a Keurig coffee maker, traditional drip coffee maker, toaster, blender, and crockpot, making meal preparation simple whether you’re staying for a few weeks or an entire season. The open kitchen allows you to stay connected with family and friends while preparing meals, making it a wonderful place to gather throughout your stay. 🌴 Relax Outdoors One of the highlights of Wotring Retreat is the private outdoor living space. Step onto the screened lanai where you’ll find comfortable seating overlooking the fully fenced backyard. The lanai enjoys shade through much of the day, making it the perfect place to enjoy your morning coffee, read a book, or unwind with a cocktail after a day of activities. The fenced backyard also offers additional outdoor seating, creating a peaceful setting for relaxing in the Florida sunshine. 🚗 Golf Cart & Parking Your stay includes a complimentary four-passenger golf cart with forward-facing seats, allowing everyone to ride together comfortably while exploring The Villages. Additional conveniences include: Private driveway parking Two-car garage (golf cart stored inside) Easy golf cart access throughout the community 🏊 Recreation & Amenities Nearby Living in Pine Ridge places you near some of the newest and most popular recreation facilities in The Villages. Pine Ridge Neighborhood Recreation Area Just minutes away you’ll enjoy: Resort-style family pool Adult pool Bocce Shuffleboard Horseshoes Recreation room Community events Lake Miona Recreation Center One of the area’s premier recreation complexes featuring: Pickleball courts Tennis courts Swimming pools Billiards Fitness classes Arts & crafts Card rooms Daily clubs and organized activities Colony Cottage Recreation Center Also nearby with additional: Pickleball Tennis Adult and family pools Recreation programs Fitness activities ⛳ Golf Paradise The Villages is home to one of the largest golf communities in the world, offering endless opportunities for every skill level. Nearby Championship Courses include: Evans Prairie Country Club Belle Glade Country Club Havana Country Club Palmer Legends Country Club You’ll also enjoy convenient access to numerous Executive Courses including Mangrove, Bonita Pass, Sweetgum, Turtle Mound, Palmetto, Tarpon Boil, and Okeechobee. 🎶 Brownwood Paddock Square Only a short golf cart ride away, Brownwood is famous for its western-inspired atmosphere, nightly live entertainment, shopping, and outstanding dining. Enjoy favorites including: Bluefin Grill & Bar Prima Italian Steakhouse City Fire McCall’s Tavern Cody’s Original Roadhouse Flying Biscuit Café Kilwins Scooples Ice Cream Spend your evenings listening to live music, dancing under the stars, or exploring the many boutiques and specialty shops. 🌅 Lake Sumter Landing Market Square Just as easily accessible by golf cart, Lake Sumter Landing offers a beautiful waterfront setting with nightly entertainment and a completely different atmosphere. Stroll along the boardwalk, enjoy waterfront dining, shop local boutiques, or visit favorites including: TooJay’s Deli RJ Gator’s Thai Ruby Amelia’s Panera Bread Starbucks Kilwins Barnes & Noble Whether you’re enjoying dinner, shopping, or simply taking in the waterfront views, Lake Sumter Landing is always worth the trip. 🛍 Shopping & Everyday Convenience Everything you need is only minutes away at nearby shopping centers including Colony Plaza and Trailwinds Village, offering: Publix Walgreens First Watch Jersey Mike’s Five Guys Beef ’O’ Brady’s Dunkin’ Banking Medical offices Additional restaurants and retail shopping 🚲 Experience The Villages Lifestyle Few places offer the lifestyle found in The Villages. During your stay you’ll enjoy: Championship Golf Executive Golf Hundreds of Pickleball Courts Tennis Bocce Recreation Centers Swimming Pools Walking & Nature Trails Hundreds of Resident Clubs Nightly Live Entertainment Golf Cart Transportation Year-round activities and events Every day offers something new to explore. 🪪 Temporary Resident IDs (Highly Recommended) Guests staying 30 days or longer are eligible to purchase Temporary Resident IDs through The Villages®. These IDs allow you to enjoy many of the exclusive amenities available to residents, including: ✔ Executive golf courses (green fees apply) ✔ Recreation centers ✔ Adult and family swimming pools ✔ Pickleball courts ✔ Tennis courts ✔ Bocce courts ✔ Recreation classes and activities ✔ Hundreds of clubs and organized events ✔ Access to many resident-exclusive amenities and programs Current Cost: Approximately $50 per person (subject to change by The Villages®). After your reservation is confirmed, AJ Home Rentals will send you the required Temporary Resident ID forms and guide you through the simple application process so your IDs are ready shortly after your arrival. 🐾 Pet Policy We welcome dogs with prior approval only. Before booking, please provide: Breed Weight Age Number of dogs Additional pet fees may apply. Cats are not permitted. Unauthorized pets may result in additional cleaning fees, damage charges, cancellation of the reservation, or removal from the property without refund. ❤️ Why Book with AJ Home Rentals? When you reserve with AJ Home Rentals, you’re choosing a locally owned and professionally managed company dedicated to providing exceptional accommodations and personalized service. 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, fully equipped homes ✔ Local recommendations to help you make the most of your visit Our goal is to provide an exceptional experience from the moment you book until the day you check out. 🚙 Complimentary Golf Cart Disclaimer Your stay includes a complimentary 4-passenger forward-facing golf cart. While we make every effort to keep it available, unforeseen maintenance or mechanical issues may occasionally occur. As the golf cart is provided as a complimentary amenity, no refunds or credits will be issued if it becomes unavailable during your stay. Drivers must be 21 years of age or older with a valid driver’s license and comply with all Florida laws and The Villages® golf cart rules. Guests assume all responsibility for the safe operation of the golf cart. The property owner and AJ Home Rentals are not responsible for any accidents, injuries, damages, losses, or claims arising from the use of the golf cart. 🌴 We Can’t Wait to Welcome You! Whether you’re visiting to play golf, discover the endless recreation opportunities, enjoy nightly entertainment, or simply relax in the Florida sunshine, Wotring Retreat offers the perfect home base for your Villages adventure. Book your stay today and experience why so many guests return to The Villages year after year!

Charo Sunshine Retreat at The Villages

The Villages, FL, US
3 Bedrooms 5 Guests
Aug 20 - 22
$114 night

Spanish-Style Charm • Live Music • The Classic Villages Lifestyle Welcome to Santiago Sunshine Retreat, a beautifully appointed 3-bedroom, 2-bathroom home located in the desirable Villages of Santiago, where classic Spanish-inspired design meets the vibrant lifestyle that makes The Villages so beloved. This home is thoughtfully designed for comfort, connection, and easy living — ideal for friends or family looking to experience everything The Villages has to offer. 🛏 Sleeping & Bathroom Layout (Split Floor Plan) Primary Suite (Owner’s Retreat) King bed Spacious walk-in closet Private en-suite bathroom Walk-in shower Double-sink vanity Bedroom Two King bed Dresser TV Bedroom Three King bed Dresser TV Guest Bathroom Full bathroom shared by Bedrooms 2 & 3 Conveniently located and well-appointed 🍽 Fully Stocked Kitchen & Inviting Living Spaces The kitchen is fully stocked for adults who enjoy cooking or baking, making it easy to prepare anything from a casual breakfast to a full dinner with friends. Complete cookware & bakeware Well-equipped kitchen with ample storage Dining area perfect for shared meals Very comfortable living room seating Large TV in the living room TVs in every bedroom This home is designed to feel relaxed, welcoming, and easy — just like life in The Villages should be. 🌿 Indoor & Outdoor Living Indoor Lanai / Flex Space Enclosed indoor lanai Desk and workspace — ideal for remote work or planning daily adventures Quiet spot to enjoy morning coffee or unwind Screened Outdoor Lanai Fully enclosed & screened-in Grill / barbecue Cozy seating area Perfect for morning coffee, sunset cocktails, or evening conversation This outdoor space invites you to slow down, enjoy the breeze, and soak in the peaceful ambiance of the neighborhood. 🎶 The Villages Lifestyle — Town Squares, Music & Activities One of the highlights of staying in the Villages of Santiago is the unbeatable access to two of The Villages’ most iconic town squares — both offering live music every afternoon and every night. 🎵 Lake Sumter Landing Waterfront town square with lively energy Live music daily & nightly Dancing under the stars Restaurants with outdoor seating and live entertainment Movie theater, shopping, and scenic sunset views A favorite destination for evening golf cart rides 🎺 Spanish Springs Elegant, Spanish-inspired architecture Live music every afternoon & evening Open-air dancing and social gatherings Restaurants and cafés with live performances Boutique shopping and classic Villages charm 🍽 Dining, Dancing & Nightlife Both town squares offer: Restaurants with live music Outdoor patios perfect for cocktails and people-watching Casual to upscale dining options Nightly dancing and community events Guests can enjoy dinner, live entertainment, and dessert — all without needing a car. 🏓 Recreation, Pickleball & Outdoor Fun In addition to the town squares, guests have access to countless activities throughout the area: Pickleball courts at nearby recreation centers Swimming pools & fitness centers Walking and biking paths Championship golf courses & practice facilities For those who enjoy quieter surroundings, the nearby more rural areas toward Belle Glade offer peaceful scenery, open landscapes, and beautiful golf cart rides — a relaxing contrast to the lively town centers. ☀️ Guest Experience & Important Notes Guidance provided on how The Villages lifestyle works, including amenities and costs Instructions for Temporary Resident ID processing (when applicable) Home dashboard with house information and local tips 🏡 House Rules Dogs allowed upon approval Cats are not allowed No smoking or vaping anywhere on the premises 🌅 Why Guests Love Santiago Sunshine Retreat Prime location near two iconic town squares Live music every single day & night Easy golf cart access to dining, entertainment, and recreation A perfect blend of vibrant social life and peaceful relaxation

Thurmond Retreat at Liberty Park in The Villages

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 20 - 25
$95 night

⭐ IMPORTANT: JAN–MAR 2027 | FULL-MONTH BOOKINGS ONLY (NO PARTIAL STAYS) ⭐ 🌟 Thurmond Retreat | Liberty Park Villa in The Villages, Florida 🌟 2-Bedroom, 2-Bathroom Villa with Golf Cart • Prime Location • Pristine Condition Welcome to Thurmond Retreat, a beautifully maintained 2-bedroom, 2-bathroom villa in The Villages, FL, located on Thurmond Avenue in the highly desirable Villages of Liberty Park. Ideally positioned between Lake Sumter Landing and Brownwood Paddock Square, this home offers easy access to golf, recreation centers, shopping, dining, and nightly live entertainment. This villa is professionally managed, meticulously cared for, and offers the same high standards and policies as all A&J Home Concierge properties. 🏡 Comfortable, Inviting Living Spaces Designed for extended stays and comfort, this open-concept villa features tasteful décor and a relaxing atmosphere throughout. The living room includes two plush recliners and a large sofa, ideal for unwinding after a full day of activities. Smart TVs with streaming capabilities allow you to enjoy your favorite shows and movies with ease. Primary Suite: King bed, private ensuite bathroom Guest Bedroom: Queen bed, comfortable and quiet Bathrooms: Two full bathrooms, clean and well appointed 🍽️ Fully Equipped Kitchen & Lanai Living The kitchen is fully stocked for everyday cooking or longer stays and includes everything needed for meal prep and entertaining. Step outside to the private screened lanai, featuring a comfortable sitting area — perfect for morning coffee, afternoon reading, or evening relaxation in the Florida breeze. 🚗 Four-Seat Golf Cart Included Explore The Villages the way locals do with the included four-seat golf cart, giving you easy access to recreation centers, pools, golf courses, shopping, and nightly entertainment — all just minutes away. 🎾 Recreation Centers, Pickleball & Endless Amenities One of the highlights of staying at Thurmond Retreat is proximity to several top Villages recreation centers, offering activities and amenities throughout the day: Nearby Recreation Centers Include: Seabreeze Recreation Center – Pools, pickleball courts, tennis courts, shuffleboard, beach tennis, ping pong, and a fitness gym (gym fee applies on-site) Additional nearby rec centers with daily classes, social clubs, arts & crafts, billiards, table tennis, and group fitness As a guest in The Villages, you’ll have access to: 70+ swimming pools throughout the community Adult-only pools for lap swimming and relaxation Family-friendly pools with social and recreational activities Hundreds of daily classes and activities, including pickleball leagues, yoga, water aerobics, dance, card games, and social clubs There is truly something happening all day, every day. ⛳ Golfers’ Paradise Enjoy access to 40+ executive golf courses and championship courses throughout The Villages, many just minutes away by golf cart. Whether you’re a casual golfer or play daily, this location offers unmatched convenience. 🎶 Live Music, Dining & Shopping Lake Sumter Landing: Waterfront dining, boutique shopping, and nightly live music Brownwood Paddock Square: Restaurants, movie theater, retail shops, and nightly entertainment Live music and dancing happen 365 days a year, making it easy to enjoy the true Villages lifestyle. Convenient shopping is nearby with Publix, Walmart Neighborhood Market, and local retail centers just minutes away. 🪪 Villages ID Information Guests may purchase Villages IDs directly from The Villages (currently $50 per ID). These IDs provide access to pools, recreation centers, classes, and amenities within this 55+ active adult community. Full instructions are provided prior to arrival. 🐾 Pet Policy Pets upon approval only No cats allowed Additional pet terms apply and must be approved prior to booking ⭐ Additional Highlights Pristine, professionally maintained home Streaming Smart TVs Four-seat golf cart included Prime Liberty Park location Jan–Mar 2027: Full-month bookings only

The Davit Place Getaway | The Villages FL

The Villages, FL, US
2 Bedrooms 4 Guests
Aug 20 - 27
$84 night

Welcome to The Davit Place Getaway, where the magic of The Villages lifestyle awaits you! Picture waking up in your cozy patio villa, stepping out onto your serene little patio to greet the warm Florida sunshine, and feeling the gentle breeze as you sip your morning coffee. This is the perfect home base for your adventures in The Villages – the world’s largest active adult community designed for fun and connection! Inside, this charming property boasts 2 spacious bedrooms, making it ideal for couples or friends traveling together. The primary suite features a luxurious King bed, perfect for unwinding after a day of excitement, while the second bedroom is furnished with a cozy Queen bed to ensure a restful night’s sleep. You’ll appreciate the convenience of 2 pristine bathrooms and a fully equipped kitchen where you can whip up your favorite meals or indulge in your own coffee bar experience. Gather in the warm living spaces, equipped with high-speed WiFi throughout – ideal for remote work, streaming your favorite shows, or connecting with family back home. Plus, you’ll enjoy two portable chairs provided for your outings to the town squares to soak up the vibrant nightly live entertainment! Living in The Villages means non-stop entertainment 365 days a year. Whether it’s live music in the squares, dance parties, golf cart parades, or themed events, there’s always something incredible happening every afternoon and evening. Just a short golf cart ride away, you have the fabulous Lake Sumter Landing, known for its beautiful waterfront and charming atmosphere. The nightly live entertainment is free and features local musicians that create an upbeat ambiance perfect for dancing and socializing. Grab a delicious meal at great spots like Cody’s Original Roadhouse, Lenny’s Bar & Grill, or Alley Cats Bar & Grill, and don’t forget to explore unique shops like The Village Merchants for that perfect souvenir. You can unwind each evening right in your portable chairs, set up at the square to catch the entertainment! For even more recreational choices, take advantage of the nearby recreation centers Hemingway Recreation Center – The closest neighborhood recreation center (about 2–3 minutes by golf cart). Adult pool Bocce Shuffleboard Horseshoes Pavilion Lake Miona Recreation Center – About 4–5 minutes away. Neighborhood recreation center Adult pool Indoor meeting/activity rooms Canal Street Pool & Recreation Center – Approximately 5–6 minutes away. Adult pool Recreation activities Savannah Recreation Center – Around 5–7 minutes away. Recreation rooms Adult pool Organized activities Churchill Street Family Pool & Recreation Center – About 6–8 minutes away. Family pool Recreation facilities Access to these centers and their amenities require Temporary Lifestyle IDs, which you will receive upon booking. Kindly complete the form for these IDs, available for pickup upon arrival for a small fee of $50, unlocking access to over 100 recreation centers, 70 pools, and 50 executive golf courses! Looking for outdoor adventures? You’re in luck! Central Florida offers fantastic options, from the thrills of Walt Disney World and Universal Studios (~1–1.5 hrs), to the natural beauty of springs like Ginnie Springs and Rainbow Springs just 30–45 minutes away. For beach lovers, the Gulf Coast is only about an hour and a half drive away, while Ocala National Forest and horse country are nearby for the nature enthusiasts. Note that, unfortunately, we do not permit pets in our villa. Ready to embark on this lovely lifestyle? Don’t hesitate to reach out with any questions before or after booking. We can’t wait for you to experience the vibrant charm of The Davit Place Getaway!

Vacation Rentals in Lady Lake by Amenities & Features

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Vacation Rentals Near Lady Lake

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