Pet-friendly vacation rentals in Wildwood, FL

Explore 29 pet-friendly vacation rentals, homes, and villas in Wildwood, FL for your next getaway or business trip. Bring your pet along and enjoy the comfort and privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking and Homes with Pools. Throughout your stay, settle in together, enjoy more space to relax, and experience your destination side by side. With options starting as low as $84 per night and homes offering up to 3 bedrooms and 3 bathrooms, it's easy to book a comfortable stay personalized for your taste. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next pet-friendly adventure and enjoy the journey together.

29 Pet-Friendly Homes in Wildwood

Atwood Signature Home | Walk to Brownwood

Wildwood, FL, US
3 Bedrooms 6 Guests
Nov 13 - 18
$120 night

Atwood Signature Home | Walk to Brownwood • Private Fenced Courtyard • Pet Friendly Welcome to Atwood Signature Home, a beautifully appointed three-bedroom, two-bath courtyard villa nestled in the highly desirable Atwood Bungalows neighborhood in the Village of Collier. Originally designed as a lifestyle model home, this professionally decorated residence combines comfort, style, and an unbeatable location, all within walking distance of Brownwood Paddock Square and Traverse Plaza. Whether you’re visiting for a month or enjoying an extended stay, Atwood Signature Home offers the perfect blend of privacy, convenience, and the vibrant lifestyle that makes The Villages® one of Florida’s most sought-after destinations. Designed for Comfortable Living Step inside to an inviting open floor plan filled with natural light, tasteful décor, and comfortable furnishings that create a warm, welcoming atmosphere throughout the home. The spacious living room offers plush seating, a large-screen TV, and plenty of room to gather with family and friends after a day of exploring The Villages. The upgraded kitchen is fully equipped with everything needed to prepare meals at home, including cookware, dishes, coffee maker, blender, toaster, and all the everyday essentials. A large walk-in pantry provides generous storage, making longer stays especially convenient. The primary suite features a luxurious king-size bed, quality furnishings, and a private ensuite bathroom designed for comfort and relaxation. Two additional guest bedrooms each offer comfortable queen-size beds, dressers, and thoughtfully appointed spaces, making the home ideal for couples, families, or friends traveling together. Additional amenities include: Complimentary high-speed Wi-Fi Central air conditioning Full-size washer and dryer Large walk-in pantry Professionally decorated interior Comfortable, high-quality furnishings throughout Your Own Private Outdoor Oasis One of the highlights of Atwood Signature Home is its large, fully fenced courtyard, providing exceptional privacy and plenty of room to enjoy the beautiful Florida weather. Relax under the covered lanai with your morning coffee, enjoy dinner outdoors, or fire up the BBQ grill for an evening cookout with family and friends. The spacious backyard offers room to unwind, entertain, or simply enjoy the peaceful surroundings, while providing a secure outdoor space for an approved dog. Walk to Everything You Need One of this home’s greatest features is its exceptional walkability. You’re just a short walk from Traverse Plaza, where you’ll find everyday conveniences including: Publix Super Market Subway Restaurants and cafés Salons and personal services Banking Medical offices Everyday shopping Pharmacies The nearby AVIV Clinic and additional healthcare providers Leave the car behind and enjoy having groceries, dining, and daily essentials just minutes from your front door. Brownwood Paddock Square Also within walking distance is the popular Brownwood Paddock Square, one of the signature town squares in The Villages and a favorite gathering place for residents and visitors alike. Brownwood offers: Live entertainment every evening, 365 days a year Outdoor dancing Seasonal festivals and community events Boutique shopping Specialty retailers Steakhouses Seafood restaurants Italian dining Mexican restaurants Pizza Wine bars Coffee shops Ice cream Casual dining Beautiful western-inspired architecture and lively atmosphere Whether you’re meeting friends for dinner, enjoying live music, or simply strolling through the square with an ice cream in hand, Brownwood truly captures the spirit of The Villages lifestyle. Recreation & Golf The home is conveniently located near several recreation centers offering: Resort-style family pools Adult pools Pickleball courts Tennis courts Bocce Fitness facilities Walking trails Clubs and daily activities Golf enthusiasts will appreciate easy access to numerous executive and championship golf courses throughout both the northern and southern areas of The Villages, making this an outstanding location for golfers looking to experience a variety of courses. Just a short drive or ride away, you’ll also enjoy: Lake Sumter Landing, featuring waterfront dining, boutique shopping, and nightly live entertainment. Edna’s on the Green, a local favorite for afternoon live music, great food, and relaxed outdoor seating. Okahumpka Recreation Area, known for its scenic walking trails, peaceful lake views, and beautiful natural surroundings. Whether your ideal vacation includes golf, swimming, shopping, live entertainment, dining, or simply relaxing in your own private courtyard, Atwood Signature Home offers the perfect place to experience everything that makes The Villages so special. Pet Policy One well-behaved dog may be considered with prior approval. Please contact us before booking if you plan to travel with a dog. Cats are not permitted.

Brownwood Lifestyle Escape

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 26
$163 night

High Season has a three-month minimum requirement 🌿 Brownwood Lifestyle Escape at Atwood Bungalows – Prime Location • Water View • Golf Cart & Bikes Included 🌿 Welcome to your dream stay in the heart of The Villages, Florida — perfectly located just steps away from Brownwood Paddock Square and in walking distance to the Aviv Clinics within The Center for Advanced Healthcare at Brownwood. This beautifully furnished three-bedroom, two-bathroom bungalow was once a model lifestyle home for The Villages, showcasing exceptional quality, comfort, and unbeatable convenience. 🏡 Perfect Location — Walk to Everything! You’ll love being walking distance to: Brownwood Paddock Square – enjoy live entertainment 365 days a year Publix & Tad Retail Shopping Center – easy access to groceries and retail shops Brownwood Hotel & Spa – indulge in relaxing spa services The Wolfgang Puck Restaurant and many other dining options Aviv Clinics in The Villages – convenient healthcare access 🚲 Home Highlights 3 Bedrooms / 2 Bathrooms King-size bed in the primary suite Two queen beds in the guest bedrooms Primary en-suite bathroom with walk-in shower, dual sinks, and walk-in closet High-quality furnishings throughout Bright, open layout with beautiful water views visible from the kitchen, living area, and lanai Outdoor seating area with BBQ grill — perfect for relaxing evenings 🌅 Sunset Water Views Enjoy a stunning, expansive pond view right in your backyard. It’s the ideal spot to unwind with a drink, watch the sunset, and soak in the peaceful atmosphere. 🏌️ Amenities for the Ultimate Villages Experience Two-seater golf cart included Two bicycles for scenic rides Folding chairs to bring to the Square for nightly live music and events Centrally located with quick golf cart access to multiple pools, recreation centers, and golf courses 🪪 Villages Lifestyle Access Temporary Resident IDs are available for a one-time $50 fee (paid directly to The Villages). This pass gives you access to: 40+ executive golf courses All neighborhood recreation centers and pools Special resident activities and amenities 🍽️ Endless Entertainment & Dining Take your golf cart or simply walk to enjoy live music, dancing, boutique shopping, and dining options ranging from casual to fine dining — all at Brownwood Paddock Square. Its central location also allows for easy access north or south to explore everything The Villages has to offer. ✨ Whether you’re here for a season or longer, this Atwood Bungalow retreat offers comfort, convenience, and a true Villages lifestyle experience.

Richmond Retreat Home

Wildwood, FL, US
3 Bedrooms 6 Guests
Sep 30 - Oct 5
$112 night

IMPORTANT !!! JAN & FEB require to be booked together / no partial bookings allowed Golf cart use optional - $12/day or $300/month - billed on separate invoice after signing applicable waiver. Experience vibrant living in the highly sought-after Village of Richmond in The Villages, FL, with this exquisite 3-bedroom, 2-bath Sequoia model designer home. 🌿 This stunning home is perfectly located just a short stroll away from both family and adult pools, ensuring that relaxation and recreation are always just steps away. Whether you’re looking to lounge by the pool or engage in friendly sports competitions, this location offers it all. 🏊‍♂️🌞 Prime Location: Situated within minutes of Brownwood Paddock Square and other local entertainment hubs, your adventures begin the moment you step out of the door. With a 4-seat golf cart at your disposal, you can easily explore nearby destinations like Sawgrass Grove, indulge in culinary delights at Edna’s on the Green, or enjoy the lively atmosphere of Everglades Recreation Center. 🚐 The home’s proximity to shopping and dining means you’re always close to essentials and entertainment. Grab groceries at Publix, enjoy a coffee or ice cream at Foxtail, or dine at nearby restaurants. 🍦☕ Recreational Heaven: For those who love staying active, you’re surrounded by a variety of activity facilities including pickleball, tennis, sand volleyball, outdoor weights, bag toss, shuffleboard, and bocce ball. 🎾🏐 There’s no shortage of ways to stay engaged and enjoy the Florida sunshine. And for golf enthusiasts, this home is at the center of it all! Surrounded by pristine golf courses, including a chip and putt course located at the Richmond South entrance, it’s a golfer’s paradise. ⛳ Inside the Home: Step into a beautifully designed space featuring an open kitchen and living area plan, ideal for entertaining guests or enjoying cozy evenings at home. The elegant lanai provides the perfect setting for outdoor enjoyment, whether you’re hosting a barbecue or just relaxing with a book. 🏡🍃 Explore The Villages: Living in the Richmond Retreat Villa means more than just a home; it’s about embracing a vibrant lifestyle. The Villages is renowned for its extensive amenities and active community life. From golf courses to pools, recreation centers, and social clubs, there’s something for everyone. Enjoy live entertainment, festive events, and endless opportunities to connect with friends and neighbors. 🎉 Don’t miss out on this chance to experience luxury living in one of Florida’s premier 55+ communities. Contact us today to make Richmond Retreat Villa your new home in paradise! 🏠🌴 Bedroom Layout: Bedroom 1: One Queen Bed (2 guests) 👑 Bedroom 2: One Queen Bed (2 guests) 🛏️ Bedroom 3: One Queen Bed (2 guests) 🛏️ This home offers everything you need for a comfortable and luxurious lifestyle in The Villages. Book a viewing today and start your new adventure! 📞

Village of Collier Retreat w/ Golf Cart & Lanai!

Wildwood, FL, US
3 Bedrooms 6 Guests
Sep 21 - 24
$248 night

Gated 55+ Community | Pets Welcome w/ Fee | Step-Free Access Golf in the morning, pool in the afternoon, and live music at Brownwood Square by sunset — this vacation rental in the heart of The Villages keeps the fun close! The 3-bedroom, 2-bath Village of Collier home is perfect for 55+ travelers, with Championship Golf Clubs nearby, top-tier amenities just a golf cart ride away, and a private patio for quiet moments. Book now and make this laid-back lifestyle yours. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed VILLAGE OF COLLIER AMENITIES - Outdoor pool w/ chairlift, lounge chairs, poolside dining area - Tennis/pickleball courts - Outdoor fireplace & grills - Bocce balls, horseshoes, shuffleboard - Pet lawn - Gated community OUTDOOR LIVING - Screened lanai w/ dining set - Golf cart (waiver may be required) INDOOR LIVING - Flat-screen TVs - Dining table - En-suite bathroom & walk-in closet in bedroom 1 KITCHEN - Refrigerator, stove/oven, dishwasher - Drip & Keurig coffee makers (coffee provided) - Toaster, toaster oven, microwave - Cooking basics, dishware & flatware, trash bags & paper towels - Breakfast bar GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Washer, dryer, laundry detergent, iron & board, hangers - Linens & towels, hair dryer FAQ - Pet fee (paid pre-trip) - 55+ community ACCESSIBILITY - Single-story home, step-free entry PARKING - Garage (1 vehicle) - Driveway (1 vehicle) - Free street parking (first-come, first-served) -- THE LOCATION -- - 1 mile to Brownwood Paddock Square - 1-4 miles to Championship Golf Clubs: Belle Glade, Bonifay, Cane Garden, Evans Prairie - 6 miles to Lake Sumter Landing - 63 miles to Orlando International Airport -- REST EASY WITH US -- Property Manager 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, 2 pets max) - 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 ADDITIONAL INFORMATION - This single-story home offers step-free entry - A waiver may be required prior to using the golf cart. If you wish to use the golf cart, please reach out to the Guest Contact after booking - This property is located in a 55+ community Licence number: DWE7000729;DWE7000729

The Osborne Getaway Home at The Villages | Golf Cart Included

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 28
$108 night

Richmond Retreat Villa Designer Home • Golf Cart Included • Walk or Ride to Brownwood • Prime Richmond Location Experience elevated Florida living in the highly sought-after Village of Richmond in The Villages, Florida. Perfectly positioned near Brownwood Paddock Square, Sawgrass Grove, Southern Oaks, championship golf, recreation centers, pools, dining, shopping, and endless entertainment, Richmond Retreat Villa offers the ideal blend of comfort, convenience, and lifestyle. Whether you’re planning a seasonal escape, an extended stay, a golf getaway, or simply looking to experience everything The Villages has to offer, this beautifully appointed designer home provides the perfect home base. Perfect location – Situated equally between Clarendon (family pool, pickleball and much more) and Richmond (adult pool, dog park, walking trails) recreation centers, 3 minute walk to each. IMPORTANT: January through March reservations require full-month bookings. Partial month reservations are not permitted during this period. Exception: possible 2 week availability first 2 weeks in February. 🏡 The Home This beautifully furnished designer home features: • 3 Bedrooms • 2 Bathrooms • Open-concept floor plan • Fully equipped kitchen • Spacious living and dining areas • High-speed Wi-Fi • Full-size washer and dryer • Private outdoor living space • Included 2-seat golf cart • While the garage is not available for vehicle parking, ample Driveway parking is provided. • The home has a doorbell camera, no other cameras inside or outside the property Designed for comfort and easy living, the bright and airy layout creates a welcoming environment for couples, families, snowbirds, and extended-stay guests alike. Large windows fill the home with natural Florida sunshine, while the thoughtfully selected furnishings create a warm, inviting atmosphere throughout. The open-concept design allows everyone to stay connected whether preparing meals, enjoying family time, entertaining friends, or simply relaxing after a day of activities. 🍳 Fully Equipped Kitchen The heart of the home is the spacious kitchen, fully equipped with everything needed for preparing meals during your stay. Features include: • Modern appliances • Ample counter space • Generous cabinet storage • Coffee maker • Cookware and kitchen essentials • Dining space for gathering and entertaining Whether you’re preparing breakfast before a round of golf or enjoying dinner after an evening at Brownwood, you’ll find everything you need. 🌴 Outdoor Living Florida living is all about enjoying the outdoors. Relax on the private lanai while: • Enjoying your morning coffee • Reading a favorite book • Dining outdoors • Entertaining family and friends • Enjoying warm Florida evenings The peaceful outdoor setting creates the perfect place to unwind and enjoy the sunshine year-round. 🛏️ Sleeping Accommodations Primary Bedroom • Queen Bed • Sleeps 2 Guest Bedroom 1 • Queen Bed • Sleeps 2 Guest Bedroom 2 • Two Twin Beds • Sleeps 2 Maximum Occupancy: 6 Guests The split-bedroom design provides privacy and comfort for everyone in your group. 🌴 Prime Richmond Location One of the greatest features of Richmond Retreat Villa is its exceptional location. Nestled in the highly desirable Village of Richmond, you’ll enjoy easy access to some of the most popular destinations in The Villages while remaining in a peaceful residential setting. Richmond places you in the perfect position to enjoy both the established favorites and the exciting growth occurring in the southern portion of The Villages. ⭐ Brownwood Paddock Square Approximately 5 Minutes by Golf Cart One of The Villages’ most popular destinations is practically at your doorstep. Brownwood Paddock Square offers: • Nightly live music and entertainment • Dancing under the stars • Restaurants and bars • Shopping and boutiques • Seasonal festivals and special events • Outdoor gathering spaces Popular nearby dining options include: • Bluefin Grill & Bar • City Fire • Prima Italian Steakhouse • Harvest Restaurant & Bar • Scooples Ice Cream Parlor Many guests enjoy taking the golf cart to Brownwood nightly to experience the unique energy and entertainment that make The Villages famous. 🍹 Edna’s on the Green Just minutes away is one of the most beloved gathering places in The Villages. Edna’s offers: • Live music • Food trucks • Outdoor bars • Social events • Relaxed outdoor atmosphere • Beautiful sunset views It’s a favorite destination for both visitors and residents. 🌅 Sawgrass Grove Another nearby entertainment destination, Sawgrass Grove offers: • Live entertainment • Outdoor dining • Food truck court • Shopping • Family-friendly events • Community gatherings ⛳ Golf Paradise Golf enthusiasts will appreciate the home’s proximity to some of The Villages’ best golf experiences. Championship Golf • Southern Oaks Championship Golf Club Executive Courses • Richmond Executive Course • Longleaf Executive Course • Red Fox Executive Course • Gray Fox Executive Course Practice Facilities • Mickylee Pitch & Putt • Driving ranges • Putting facilities Whether you’re an avid golfer or simply looking to enjoy a few rounds during your stay, you’ll find endless opportunities nearby. 🏊 Recreation Centers & Pools Richmond offers convenient access to some of the newest and most impressive recreation facilities in The Villages. Nearby recreation centers include: • Everglades Recreation Center • Ezell Recreation Center • Homestead Recreation Center • Aviary Recreation Center • Franklin Recreation Center Enjoy: • Pickleball • Tennis • Bocce Ball • Shuffleboard • Cornhole • Volleyball • Fitness classes • Walking clubs • Organized social activities The home is also conveniently located near both family and adult pools. 🚲 Walking & Nature Trails The Richmond area is known for beautiful outdoor spaces and scenic walking opportunities. Enjoy: • Neighborhood walking paths • Golf cart trails • Nature areas • Beautifully landscaped streets • Scenic biking routes Perfect for morning walks, evening strolls, and enjoying Florida’s beautiful weather. ☕ Shopping & Daily Conveniences Everything you need is just minutes away. Nearby conveniences include: • Publix • Foxtail Coffee • Walgreens • Banking services • Medical facilities • Casual and fine dining • Ice cream shops • Boutiques and retail shopping 🎟️ Temporary Resident IDs To help guests enjoy the full Villages experience, we assist eligible guests with obtaining Temporary Resident IDs through The Villages Guest ID program. Temporary Resident IDs may provide access to: • Recreation centers • Family and adult pools • Executive golf courses (greens fees may apply) • Pickleball courts • Tennis courts • Bocce courts • Organized recreation activities Please note: • Temporary Resident ID fees are established by The Villages and paid separately. • We assist with the registration process. • Early submission of guest information is encouraged. 🛺 Golf Cart Included The included 2-seat golf cart allows you to fully embrace The Villages lifestyle. Cruise conveniently to: • Brownwood Paddock Square • Sawgrass Grove • Edna’s on the Green • Southern Oaks • Recreation centers • Pools • Shopping and dining A signed golf cart waiver is required prior to receiving access to the golf cart. 🐾 Pet Policy We know pets are family too. • Small dogs may be considered with prior approval. • Approval must be obtained before booking. • Additional fees and requirements may apply. • Cats are not permitted. • Unauthorized pets may result in additional charges and/or cancellation of the reservation. Please contact us before booking if you wish to bring a dog. 🚭 House Rules For the comfort of all guests: • No smoking • No vaping • No parties or events • No illegal substances Smoking or vaping inside the home, lanai, garage, or anywhere on the property is strictly prohibited. The home has a doorbell camera, no other cameras inside or outside the property. 📶 Stay Connected The home includes high-speed Wi-Fi, making it easy to: • Stream your favorite shows • Work remotely if needed • Stay connected with family and friends • Plan your daily adventures ✨ Experience The Villages Lifestyle Richmond Retreat Villa is more than a place to stay—it’s your gateway to everything that makes The Villages one of Florida’s most sought-after destinations. Enjoy championship golf, recreation centers, pools, live music, restaurants, shopping, outdoor activities, social events, and endless opportunities to explore. Whether you’re seeking relaxation, recreation, or a little bit of both, Richmond Retreat Villa offers the perfect setting to create unforgettable memories in The Villages. Book your stay today and experience the very best of Florida living.

Navy Hill Vacation Residence (Richmond)

The Villages, FL, US
3 Bedrooms 4 Guests
Dec 5 - 17
$136 night

Please note: Feb open for the second half of the month and March require full-month bookings. Partial month stays are not available during this period. Experience vibrant living in the highly sought-after Village of Richmond in The Villages, FL, with this exquisite 3-bedroom, 2-bath designer home. 🌿 This stunning home is perfectly located just a short stroll away from both family and adult pools, ensuring that relaxation and recreation are always just steps away. Whether you’re looking to lounge by the pool or engage in friendly sports competitions, this location offers it all. 🏊‍♂️🌞 Prime Location: Situated within minutes of Brownwood Paddock Square and other local entertainment hubs, your adventures begin the moment you step out of the door. You can also explore nearby destinations like Sawgrass Grove, indulge in culinary delights at Edna’s on the Green, or enjoy the lively atmosphere of Everglades Recreation Center. 🚐 The home’s proximity to shopping and dining means you’re always close to essentials and entertainment. Grab groceries at Publix, enjoy a coffee or ice cream at Foxtail, or dine at nearby restaurants. 🍦☕ Recreational Heaven: For those who love staying active, you’re surrounded by a variety of activity facilities including pickleball, tennis, sand volleyball, outdoor weights, bag toss, shuffleboard, and bocce ball. 🎾🏐 There’s no shortage of ways to stay engaged and enjoy the Florida sunshine. And for golf enthusiasts, this home is at the center of it all! Surrounded by pristine golf courses, including a chip and putt course located at the Richmond South entrance, it’s a golfer’s paradise. ⛳ Inside the Home: Step into a beautifully designed space featuring an open kitchen and living area plan, ideal for entertaining guests or enjoying cozy evenings at home. The elegant lanai provides the perfect setting for outdoor enjoyment, whether you’re hosting a barbecue or just relaxing with a book. You have a relaxing view of two beautiful and big Spanish Moss trees in view of your lanai. 🏡🍃 Explore The Villages: Living in the Richmond Retreat Villa means more than just a home; it’s about embracing a vibrant lifestyle. The Villages is renowned for its extensive amenities and active community life. From golf courses to pools, recreation centers, and social clubs, there’s something for everyone. Enjoy live entertainment, festive events, and endless opportunities to connect with friends and neighbors. 🎉 Don’t miss out on this chance to experience luxury living in one of Florida’s premier 55+ communities. Contact us today to make Richmond Retreat Villa your new home in paradise! 🏠🌴 Bedroom Layout: Bedroom 1: One King Bed (2 guests) 👑 Bedroom 2: One Queen Bed (2 guests) 🛏️ Bedroom 3: One Queen Bed (2 guests) 🛏️ This home offers everything you need for a comfortable and luxurious lifestyle in The Villages. Book a viewing today and start your new adventure! 📞

Piper’s Nature Escape (Deluna)

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 26
$118 night

IMPORTANT! JAN-MAR 2026 only full month bookings. For monthly rates from May to October (discounted rate) please send an inquiry. Nature View | Three Recliners | Golf Cart | Bicycles | Dog Friendly 🌿 Piper’s Nature Escape (DeLuna) – Relax, Explore, & Soak In the Serenity 🐢☕🎶 Welcome to Piper’s Nature Escape, a beautifully styled 3-bedroom, 2-bathroom courtyard villa in the Villages of DeLuna—where peace and nature meet convenience and vibrant community life. This fresh, light-filled retreat is perfect for morning coffees with turtles, relaxing evenings on the lanai, and spontaneous golf cart adventures to music, food, and fun. 🛏 Villa Highlights: Fresh, Clean, and Relaxed King Bed in the master suite Queen Beds in both guest bedrooms ✨ Decorated in calming blue tones to give you a coastal-meets-spa vibe from the moment you walk in 🛁 Two full bathrooms, sparkling clean and updated 🍳 Fully equipped kitchen with all essentials to make meals at home a breeze 🛋 Almost everything is new – from décor to appliances! 🐾 Dog-friendly upon approval (Please inquire with details: breed, weight, house training status, and shedding info) 🚪 Fully fenced courtyard for privacy and peace of mind 🌞 Serene lanai with views of the pond, turtles, birds, and Florida nature at its finest—quiet, private, and a daily show of natural beauty 🚲 Two adult bicycles for scenic rides 🪑 Chairs included to bring along for nightly entertainment at the squares and rec centers 🛺 Two-seater golf cart included (waiver required) 📍 Amazing Location – Heart of North & South Piper’s Nature Escape places you in a sweet spot—ideal for relaxing or adventuring, with: Easy access to the Turnpike – only 1 hr 10 min to Orlando Airport or Disney Walk, bike, or golf cart to: Deluna Pool & Pickleball Courts Waterlily Recreation Center – featuring a family pool, bocce, pool tables, pickleball, and more! Beautiful bike trails right within DeLuna for morning rides or evening strolls Short golf cart ride to: 🎤 Brownwood Paddock Square – Enjoy live bands every night, movie theater, shopping, food, drinks, dancing, and festivals 🎶 Edna’s on the Green – A favorite local spot with live music daily, great food trucks, and shaded outdoor dining and dancing ⛳️ Golf, Recreation & Villages Fun With a Villages Temporary Resident ID ($50, paid directly to The Villages), you gain: Access to 40+ executive golf courses and championship courses throughout The Villages Entry to hundreds of activities and clubs at the recreation centers Use of resort-style and family pools across the community 🛺 Golf cart use included with booking (waiver and rules apply). Everything’s within reach—from groceries to dancing under the stars. ☕️ Why You’ll Love Piper’s Nature Escape This home captures that Florida dream life—start your mornings sipping coffee in the lanai, watching turtles glide through the pond, or listen to the breeze rustling through the trees. In the evenings, ride your cart to Brownwood for dancing or Edna’s for live music. It’s peaceful, connected, and endlessly relaxing. And with a fully fenced yard, it’s a great spot to bring your pup (with approval) and enjoy a stay that truly feels like home—just a little better. 🏡 Ready to Host You Whether you’re planning a couple’s escape, a family visit, or a stay with friends, Piper’s Nature Escape is a clean, bright, and comfortable home base to explore everything The Villages has to offer. From morning wildlife to night-time tunes, you’ll be living the life from sunrise to sunset.

Dutchess Designer Experience

The Villages, FL, US
3 Bedrooms 5 Guests
Sep 21 - 26
$102 night

Dutchess Designer Experience | Golf Cart Included | Near Lake Sumter Landing & Brownwood Welcome to Dutchess Designer Experience, a beautifully appointed 3-bedroom, 2-bath designer home nestled in the sought-after Village of St. Charles. Thoughtfully designed for comfort, relaxation, and making the most of everything The Villages® has to offer, this home is the perfect destination for couples, golfers, snowbirds, remote workers, and extended stays. From the moment you arrive, you’ll appreciate the bright, open floor plan, tasteful décor, and inviting atmosphere that makes it easy to settle in and feel at home. Whether you’re spending your days golfing, exploring the community by golf cart, enjoying nightly live entertainment, or simply relaxing on the lanai with your morning coffee, Dutchess Designer Experience is your ideal home base. The Home The spacious living room offers comfortable seating and a large Smart TV, creating the perfect gathering place after a day of adventure. Every bedroom also features its own TV, allowing everyone to unwind with their favorite shows in privacy. The fully equipped kitchen provides everything you need to prepare anything from a quick breakfast to a gourmet dinner and opens to an oversized dining area that’s perfect for family meals, entertaining friends, or enjoying game night together. Sleeping Arrangements Primary Suite King bed Smart TV Spacious walk-in closet Luxurious ensuite bathroom Dual vanities Large walk-in shower Guest Bedroom Queen bed Smart TV Flex Room / Office Dedicated office space Twin XL sleeper sofa Perfect for remote work or an additional guest Outdoor Living One of the highlights of the home is the inviting screened lanai, designed for enjoying Florida’s beautiful weather year-round. Enjoy: Outdoor dining table Comfortable modern rocking chairs Peaceful setting for morning coffee Relaxing evenings after a day of exploring The Villages A complimentary Evolution golf cart is included, making it easy to experience the community just like a local. Discover The Villages Lifestyle One of the greatest advantages of staying at Dutchess Designer Experience is its outstanding location. You’re just minutes from two of The Villages’ most popular town squares, along with recreation centers, executive golf courses, shopping, dining, and endless entertainment. Lake Sumter Landing Lake Sumter Landing is one of the most popular destinations in The Villages, offering waterfront dining, boutique shopping, seasonal events, and FREE live entertainment every evening, 365 days a year. Enjoy favorites such as: Chop House at Lake Sumter The Angler’s Club City Fire Redsauce American Italian RJ Gator’s Florida Sea Grill & Bar Thai Ruby VKI Japanese Steakhouse Cody’s Original Roadhouse TooJay’s Deli Flying Biscuit Café Starbucks Boutique shopping, ice cream shops, bakeries, wine bars, and more Whether you’re enjoying dinner by the water, listening to live music, or simply strolling through the square, Lake Sumter Landing offers something for everyone. Brownwood Paddock Square Just a short golf cart ride away, Brownwood Paddock Square features a charming western-inspired atmosphere with nightly entertainment, shopping, festivals, farmers markets, and fantastic restaurants. Popular dining options include: Bluefin Grill & Bar Wolfgang Puck Kitchen + Bar Prima Italian Steakhouse McCall’s Tavern Scooples Ice Cream Brownwood is also home to concerts, holiday celebrations, car shows, art festivals, and year-round community events. Recreation & Activities The Villages is world-famous for its active lifestyle, with something happening every day. Nearby Recreation Centers St. Charles Recreation Center Adult swimming pool Bocce Shuffleboard Horseshoes Walking areas Outdoor gathering spaces Colony Cottage Regional Recreation Center Pickleball courts Tennis courts Billiards Arts & crafts Card rooms Fitness activities Meeting rooms Numerous social clubs Lake Miona Regional Recreation Center Resort-style pool Pickleball Tennis Billiards Ping pong Fitness classes Daily activities and organized events Throughout The Villages you’ll also enjoy access to: Dozens of swimming pools Hundreds of pickleball courts Tennis complexes Bocce courts Walking and biking trails Softball fields Recreation centers throughout the community More than 3,000 clubs and organized activities covering virtually every hobby and interest imaginable. Golf Golf enthusiasts will love having several executive golf courses just minutes away, including: Bonita Pass Turtle Mound Bacall Yankee Clipper Championship golf courses, driving ranges, practice facilities, and golf academies are also conveniently located throughout The Villages. Temporary Resident IDs Guests have the opportunity to obtain two Temporary Resident IDs for their household, allowing access to many of The Villages’ outstanding recreational amenities during their stay. A one-time $50 household registration fee applies for the Temporary Resident IDs. Once your IDs have been issued, Guest Passes may also be requested for visitors in accordance with The Villages’ policies. Pet Policy We understand that dogs are family members too. Dogs are welcome with prior approval only. Breed, size, age, and house-training information may be requested before approval. Cats are not permitted. Unauthorized pets may result in additional cleaning or damage charges. Golf Cart Disclosure A complimentary Yamaha golf cart is provided for your enjoyment during your stay. While every effort is made to keep the golf cart available and in excellent operating condition, availability cannot be guaranteed due to unforeseen maintenance, mechanical repairs, manufacturer recalls, accidents, weather-related issues, or circumstances beyond our control. The golf cart is provided as a complimentary amenity and is not considered part of the rental rate. Therefore, refunds or credits cannot be provided should the golf cart become unavailable before or during your stay. Guests are responsible for operating the golf cart safely, ensuring all occupants are properly seated, and following all applicable Florida laws and The Villages community rules. We look forward to welcoming you to Dutchess Designer Experience and helping you create unforgettable memories while enjoying everything that makes The Villages® one of Florida’s premier destinations.

Charity Corner Villa at Richmond

The Villages, FL, US
2 Bedrooms 4 Guests
Sep 21 - 26
$101 night

Winter season (Dec–Apr) tends to book quickly, so monthly stays are preferred. Shorter visits may still be possible depending on our calendar—just reach out and we’ll be happy to check! NOTE: February will not be booked without January. If you book we will have to cancel the booking. 🌺 Charity Corner Villa at Richmond – Peaceful Views & Prime Location Near Brownwood Welcome to Charity Corner Villa at Richmond, a beautifully designed 2-bedroom, 2-bathroom villa perfectly situated in the sought-after Villages of Richmond community — just five minutes by golf cart from Brownwood Paddock Square. This bright and inviting home offers modern comfort, open living spaces, and the ideal location to enjoy all that The Villages lifestyle has to offer. 🏡 Inside the Home This villa features a thoughtful split floor plan, offering privacy and comfort for you and your guests. The primary suite is located at the back of the home, while the guest bedroom is at the front — perfect for visiting family or friends. Fully equipped kitchen with full-size appliances, cookware, utensils, coffee maker, and all essentials for easy at-home dining. Dining area with a six-seat table — perfect for relaxing meals or morning coffee. Spacious living room with cozy reclining sofas and a large flat-screen TV, perfect for unwinding after a day of exploring. Primary bedroom with a king-size bed, private ensuite bathroom, and TV for added comfort. Guest bedroom with a queen-size bed and convenient access to the second full bathroom. The villa comes stocked with linens, towels, and household essentials so you can settle in and start enjoying your stay right away. 🌿 Outdoor Living Enjoy your morning coffee or evening drink on the screened lanai, overlooking a wide green space with no rear neighbors. As a corner villa, you’ll have extra privacy and an open, airy feel. A golf cart and golf cart garage are included for your use, making it easy to explore all that The Villages has to offer. 🎵 Location Highlights – The Villages of Richmond Located just steps from Brownwood Paddock Square, this villa places you in the heart of entertainment, recreation, and dining in The Villages: Brownwood Paddock Square – Only a 5-minute golf cart ride away! Enjoy nightly live music, popular restaurants like City Fire, Harvest Restaurant, and Bluefin Grill & Bar, plus boutique shops, a movie theater, and the Brownwood Hotel & Spa. Richmond Pitch & Putt Golf Course and community pool are just around the corner for recreation and fun. Harry & The Natives Restaurant – A must-visit new spot overlooking Lake Okahumpka with live music, great food, and lakefront views. Nature trails nearby for peaceful morning or afternoon walks. Edna’s on the Green – About 10 minutes away by golf cart, featuring outdoor dining, live music, and a laid-back, Florida-style atmosphere. Lake Sumter Landing – About 20 minutes away by golf cart for additional shopping, dining, and live entertainment. Eastport (coming soon) – A brand-new destination for recreation, dining, and music, just 15 minutes away. ⛳ Your Villages Experience Guests can purchase a Temporary Resident ID ($50 per couple, paid directly to The Villages) for access to over 40 executive golf courses, multiple recreation centers, pools, and hundreds of social clubs and events happening year-round. With nightly entertainment in the squares 365 days a year, there’s always something to enjoy! ✨ Summary 2 Bedrooms | 2 Bathrooms | Sleeps 4 King bed in master | Queen bed in guest room Split floor plan for privacy Fully equipped kitchen 6-seat dining area Reclining sofas | Smart TVs Screened lanai with open green view (no rear neighbors) Corner villa | Golf cart garage & golf cart included Linens, towels, and essentials provided 5 min to Brownwood | 10 min to Edna’s | 15 min to Eastport | 20 min to Lake Sumter Charity Corner Villa at Richmond combines the best of comfort, convenience, and lifestyle — offering a quiet retreat with a beautiful view, all just minutes from the heart of The Villages’ entertainment and activities.

Deauville Comfort Retreat

The Villages, FL, US
3 Bedrooms 5 Guests
Sep 30 - Oct 5
$126 night

Village of Charlotte | The Villages, Florida Welcome to Deauville Comfort Retreat, a beautifully appointed 3-bedroom, 2-bath home nestled in the desirable Village of Charlotte, one of the most convenient and sought-after locations in The Villages. Designed for relaxation and comfort, this inviting home offers everything you need for an unforgettable Florida getaway. From the moment you arrive, you’ll appreciate the spacious open floor plan, comfortable furnishings, and thoughtful amenities throughout. Whether you’re visiting to golf, explore the community, enjoy nightly entertainment, or simply relax in the Florida sunshine, Deauville Comfort Retreat is the perfect place to call home. One of the home’s most popular features is the large climate-controlled enclosed lanai, providing an additional living space that can be enjoyed comfortably year-round. Enjoy your morning coffee, read a good book, gather with friends, or unwind after a day of golf in this bright and inviting space. Even better, you’ll have the convenience of a complimentary 2-seat electric golf cart, making it easy to explore everything The Villages has to offer. Best of all, you’re located just 12 minutes from Lake Sumter Landing and 13 minutes from Brownwood Paddock Square, giving you quick access to dining, shopping, golf, recreation, and FREE nightly live entertainment. The Home 3 Bedrooms | 2 Bathrooms King Bed in the Primary Suite Queen Bed in Guest Bedroom #1 Queen Bed in Guest Bedroom #2 Spacious open-concept floor plan Climate-controlled enclosed lanai with plenty of comfortable seating Complimentary 2-seat electric golf cart Fully equipped kitchen Breakfast bar with seating Dining area Comfortable reclining sofas in the living room Smart TV in the Living Room Smart TV in the Primary Bedroom High-speed Wi-Fi Full-size washer & dryer Two-car garage Primary Suite Retreat to the spacious primary suite featuring a comfortable King-size bed, Smart TV, large walk-in closet, double sink vanity, walk-in shower, and private ensuite bathroom. It’s the perfect place to relax after a day of enjoying The Villages. Guest Bedrooms Both guest bedrooms are thoughtfully furnished with Queen-size beds, comfortable mattresses, ample closet space, and tasteful décor to ensure every guest enjoys a restful night’s sleep. The guest bathroom features a convenient tub/shower combination, making it ideal for families or extended stays. Fully Equipped Kitchen Whether you’re preparing breakfast before heading to the golf course or cooking dinner after an evening at the town squares, you’ll find everything you need. The kitchen includes: Full-size refrigerator Range & oven Microwave Dishwasher Coffee maker Cookware Bakeware Dinnerware Glassware Utensils Small appliances Plenty of counter space and storage Climate-Controlled Enclosed Lanai The enclosed lanai quickly becomes everyone’s favorite gathering place. Enjoy: Comfortable seating Air-conditioned comfort year-round Morning coffee Afternoon reading Evening cocktails Family game nights Additional living space regardless of Florida weather It’s the perfect extension of the home and a wonderful place to relax any time of day. Explore The Villages Located in the Village of Charlotte, you’ll enjoy quick access to many of The Villages’ most popular destinations. Championship & Executive Golf Golf enthusiasts will appreciate being just minutes from several outstanding golf facilities, including: Bonifay Country Club Evans Prairie Country Club Havana Country Club Sarasota Golf Practice Center Dozens of Executive Golf Courses throughout The Villages Whether you’re an experienced golfer or just beginning, you’ll find courses suited for every skill level. Recreation Centers Nearby recreation centers include: SeaBreeze Regional Recreation Center Truman Recreation Center Colony Cottage Recreation Center Enjoy: Resort-style swimming pools Pickleball Tennis Bocce Fitness centers Walking clubs Arts & crafts Billiards Cards Social clubs Daily organized activities With hundreds of clubs and activities available throughout the community, there’s always something new to experience. Town Squares Lake Sumter Landing Just 12 minutes away One of the most popular destinations in The Villages, Lake Sumter Landing offers waterfront dining, boutique shopping, live music every evening, a movie theater, scenic walking paths, and countless opportunities to relax and enjoy the atmosphere. Brownwood Paddock Square Only 13 minutes away Brownwood offers a lively western-inspired atmosphere with outstanding restaurants, boutique shopping, dancing, live entertainment every night, seasonal events, and one of the most vibrant entertainment districts in The Villages. Both town squares feature FREE live entertainment 365 nights a year, creating a true vacation atmosphere every evening. Shopping & Everyday Conveniences Everything you need is just minutes away, including: Publix Colony Plaza Shopping Center Walmart Neighborhood Market Walgreens CVS Pharmacy Banking Medical offices Hair salons UPS Store Fresh Market Local boutiques and specialty shops Popular Nearby Restaurants Enjoy some of The Villages’ favorite dining destinations, including: Bluefin Grill & Bar Belle Glade Country Club Bonifay Country Club Evans Prairie Country Club Chop House at Lake Sumter City Fire McCall’s Tavern Cody’s Original Roadhouse First Watch Panera Bread TooJay’s Deli Bonefish Grill Whether you’re looking for a casual lunch, waterfront dining, or a special evening out, you’ll have countless options nearby. Endless Entertainment The Villages is known as one of America’s premier active adult communities, offering entertainment every day of the year. During your stay, enjoy: FREE nightly live entertainment Championship and executive golf Resort-style recreation centers Pickleball and tennis Walking and biking trails Community festivals Outdoor concerts Farmers markets Car shows Performing arts Shopping Dining Hundreds of clubs and social activities No matter how long your stay, you’ll discover something new to enjoy each day. Included With Your Stay Complimentary 2-seat electric golf cart Climate-controlled enclosed lanai High-speed Wi-Fi Smart TVs Reclining living room seating Fully equipped kitchen Full-size washer & dryer Premium linens Bath towels Starter amenities Whether you’re planning a relaxing escape, an extended winter stay, or a golf vacation with friends, Deauville Comfort Retreat offers the perfect combination of comfort, convenience, and location. We look forward to welcoming you and helping you create wonderful memories in beautiful The Villages, Florida.

Golf Cart & Pool Access: The Villages Home!

Wildwood, FL, US
3 Bedrooms 6 Guests
Oct 4 - 6
$230 night

Book this vacation rental in The Villages for your next Florida getaway! This 3-bedroom, 2-bath home boasts a spacious living area and a convenient location near the Manatee Pool & Recreation Center, making it easy to enjoy a blend of recreation and relaxation. Looking to venture farther out? Take the provided golf cart to Brownwood Paddock Square and unwind while watching live music. Afterward, dine al fresco in the privacy of the screened porch. A blissful escape awaits! -- THE PROPERTY -- 0.3 Mi to Manatee Pool & Recreation Center | Private Patio | Screened Porch Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin XL Beds (Convertible to King Bed) | Additional Sleeping: Queen Air Mattress COMMUNITY AMENITIES (additional fee, paid on-site): Outdoor pools, tennis, bocce & pickleball courts, shuffleboard, cornhole, golf courses, fitness centers, recreation centers MAIN FEATURES: Flat-screen TVs, laptop-friendly workspace, dining table, walk-in closet, open floor plan, outdoor dining area KITCHEN: Stove/oven, refrigerator, dishwasher, Keurig coffee maker, microwave, cooking basics, trash bags/paper towels GENERAL: Free WiFi, central heating & A/C, washer/dryer, iron/board, linens/towels, hair dryer, keyless entry FAQ: 3 exterior security cameras (facing out), pet fee (paid pre-trip), golf cart (waiver may be required) ACCESSIBILITY: Single-story home, step-free entry PARKING: Garage (2 vehicles), driveway (3 vehicles) -- THE LOCATION -- THE VILLAGES: Colony Plaza (3 miles), Brownwood Paddock Square (3 miles), Magnolia Plaza (7 miles), Lake Sumter Landing Market Square (9 miles), GatorWorld Florida (9 miles), Spanish Springs Town Square (9 miles), Uncle Donald’s Farm (11 miles) GOLF COURSES: Sarasota Golf Practice Center (0.9 miles), Bonifay Golf Course (1 mile), Belle Glade Golf & Country Club (2 miles), Evans Prairie Golf and Country Club (2 miles), Truman Executive Golf Course (3 miles), Roosevelt Executive Golf Course (3 miles), Southern Oaks Championship Golf Course (7 miles), Lowlands Executive Golf Course (8 miles) OUTDOOR RECREATION: Manatee Pool & Recreation Center (0.3 miles), Lake Okahumpka Park (4 miles), Aviary Recreation Center and Pool (6 miles), Lake Griffin State Park (6 miles), Ezell Regional Recreation Center (7 miles), Lake Harris (18 miles), Lake Panasoffkee (19 miles), Silver Springs State Park (30 miles) DAY TRIPS: Mount Dora Historic District (25 miles), Crystal River (50 miles), Walt Disney World Resort (53 miles), Universal Studios Florida (54 miles), Orlando (54 miles), Daytona Beach (76 miles), Tampa (79 miles), Clearwater Beach (103 miles), Cape Canaveral (107 miles) AIRPORT: Orlando International Airport (61 miles) -- REST EASY WITH US -- Property Manager 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 - Dog friendly w/ $50 fee (+ fees & taxes, no cats) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home offers step-free entry - NOTE: A waiver may be required prior to using the golf cart - NOTE: No cats are allowed at the property due to the homeowner’s severe allergies. Please include any questions/requests regarding ADA-certified service animals prior to booking - NOTE: The community amenities are available for an additional fee of $50 per couple, which can be paid on-site upon arrival - NOTE: Your safety matters. This property features 3 exterior security cameras: 1 camera is located on the corner of the home facing the driveway/garage, 1 camera is located on the front door facing the front outdoor entry, and 1 camera is located on the back entrance facing the patio/back of the home. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion Licence number: DWE7000511;DWE7000511

Fieldbrook Cozy Designer Home (Pinellas)

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 26
$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! 🏡🌴

Cameo Tiki Bar Escape (Richmond)

Wildwood, FL, US
3 Bedrooms 6 Guests
Nov 7 - 12
$118 night

🌴 Welcome to The Tiki Bar Escape at the Villages of Richmond – Your Getaway in The Villages, FL! 🏡🍹 Discover your perfect Florida escape at The Tiki Bar Escape, a 3-bedroom, 2-bathroom cottage home nestled in the vibrant and growing Villages of Richmond neighborhood—just 5 minutes by golf cart from Brownwood Paddock Square! Designed for comfort, fun, and relaxation, this colorful retreat is the ideal base to experience all that The Villages lifestyle has to offer. 🛏️ Home Features & Amenities: Spacious Master Suite with a luxurious King bed and en-suite bathroom. Guest Bedroom with a cozy Queen bed – perfect for family or friends. Third Bedroom with a Twin trundle bed (sleeps 2) – ideal for visiting grandkids. Comfortable living room with a large flat-screen TV—perfect for relaxing nights in. Fully equipped kitchen with modern appliances, cookware, and essentials. Dog-friendly for one small, well-behaved dog (prior approval required). Electric 4-Seater Golf Cart – explore The Villages in classic style. Tiki Bar in the Lanai – your own private tropical lounge space. Two BBQ grills in the backyard for fun cookouts and evening gatherings. 🎶 Live Where It’s All Happening – Richmond & Surroundings Just 5 minutes by golf cart from Brownwood Paddock Square, where you’ll enjoy: Nightly live music and dancing Western-themed shops and restaurants Weekly farmers markets, festivals, and seasonal events Also near: Sawgrass Grove – local vendors, McGrady’s Pub, and another live music venue Lake Sumter Landing & Spanish Springs – scenic town squares for boutique shopping, waterfront dining, and entertainment 🏊‍♀️ Recreation & Relaxation Right Nearby Enjoy easy access to multiple recreation centers and amenities: Richmond Neighborhood Recreation Center – adult pool, pickleball, bocce, walking trails, and scenic preserves Okahumpka Recreation Center – lakeside views, kayak outings, and the soon-to-open Harry and the Natives waterfront restaurant Ezell Regional Recreation Center – indoor/outdoor fitness facilities, sports courts, arts, and clubs Everglades Regional Rec Center – one of the largest rec centers in The Villages with endless activities and social spaces Beautiful walking and biking trails wind through the Villages of Richmond, perfect for morning strolls or afternoon exploration. ⛳ A Golfer’s Paradise This home is centrally located to some of the best golf The Villages has to offer: Richmond Pitch & Putt Course – just 5 minutes by golf cart Clifton Cove Putting Course Southern Oaks Championship Golf Course Over 40 Executive Golf Courses available across The Villages With a Temporary Resident ID ($50 fee per couple, paid directly to The Villages), guests can enjoy access to all executive courses, pools, rec centers, and more. 🛍️ Shopping, Dining & Everyday Essentials Magnolia Plaza – Publix, gas station, dining, and services (golf cart accessible) Sawgrass Grove Market Area Nearby shopping centers including Colony Plaza, Southern Trace, and Trailwinds Village 🚗 Explore Central Florida & Beyond Richmond offers convenient access to the Florida Turnpike for easy day trips to: Disney World, Universal Studios, SeaWorld – just over an hour away Rainbow Springs, Crystal River, Silver Springs – for kayaking, tubing, and springs Historic towns and Florida state parks perfect for weekend adventures 🎉 Stay Longer & Save! Ask about our special monthly rates from May through October—ideal for snowbirds, seasonal stays, or extended Florida getaways. 🚭 Community Policies Non-smoking home One small dog permitted (with prior approval only) Guests must be 55+ or accompanied by someone who is. 🏝️ The Tiki Bar Escape at the Villages of Richmond – Where Every Day Feels Like a Vacation! Whether you’re here to golf, dance under the stars, relax poolside, or enjoy cocktails at your private Tiki Bar, this colorful home puts you right in the heart of everything The Villages has to offer—north and south!

Private Pool & Lake Views: Family Home in Oxford

The Villages, FL, US
3 Bedrooms 10 Guests
Sep 21 - 26
$333 night

Spend your next Florida family getaway with a stay at this beautiful 2-story house with a lake view and a large swimming pool! This 3-bedroom, 3-bath Oxford vacation rental features a private backyard, furnished screened porch, and just a short walk from Lake Miona which includes a playground, beach, and boat ramp! Explore shops and restaurants around nearby Lake Sumter Landing, check out kayaking at Lake Griffin State Park, or plan a day trip to Disney or Universal Studios while in town! -- THE PROPERTY -- Fireplace | Screened Porch | 2 Mi to Lake Sumter Landing | Water Views Bedroom 1: California King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin Beds | Living Room: 2 King Air Mattresses INDOOR LIVING: Smart TVs, board games, books, dining table, walk-in closet, en-suite bathroom, walk-in showers, garden tubs, ceiling fans OUTDOOR LIVING: Private pool, spacious deck, patio seating, outdoor dining, rocking chairs, basketball goal, fire pit KITCHEN: Refrigerator, drip coffee maker, stove/oven, microwave, dishwasher, toaster oven, kitchen island, dishware & flatware, cooking basics GENERAL: Self check-in, free WiFi, central heating & A/C, washer & dryer, laundry detergent, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryer FAQ: Pet fee (paid pre-trip) ACCESSIBILITY: 2-story house, 2 steps required to enter, interior stairs required to reach all bedrooms on 2nd floor PARKING: Carport (3 vehicles), driveway (8 vehicles), RV parking allowed (electrical hookups on-site) -- THE LOCATION -- NEARBY ATTRACTIONS: Lake Sumter Landing (2 miles), Spanish Springs Town Square (6 miles), Brownwood Paddock Square (7 miles), Venetian Gardens (14 miles) OUTDOOR FUN: Lake Miona Park & Boat Ramp (0.3 miles), Lake Miona Park (0.3 miles), Lake Griffin State Park (10 miles), Eaton's Beach at Lake Weir (12 miles) HIT THE LINKS: Lopez Legacy Golf & Country Club (6 miles), Hacienda Hills Golf & Country Club (6 miles) FLORIDA DAY TRIPS: Universal Studios (57 miles), Disney World (58 miles), Downtown Orlando (58 miles) AIRPORTS: Leesburg International Airport (18 miles), Orlando International Airport (65 miles) -- REST EASY WITH US -- Property Manager 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/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story house only requires 2 steps to enter, an interior staircase is required to reach all of the home’s bedrooms on the 2nd floor - NOTE: This property sleeps 6 guests in 5 beds, with room for 10 total by using the air mattresses

Dog-Friendly Home in The Villages w/ Private Patio

The Villages, FL, US
2 Bedrooms 4 Guests
Oct 27 - 30
$130 night

Find your bliss in The Villages at this 2-bedroom, 2-bathroom vacation rental. Whether you find yourself lounging on the private patio with your latest read, lazing alongside the community pool, or competing on the community golf course, this single-story house will provide the ideal, sun-dappled stay. Stroll through the scenic Sharon Rose Wiechens Preserve, experience the majesty of The Mammoth Live Oak Tree, or meet the creatures of Gatorland. No matter the season, exploration awaits! -- THE PROPERTY -- Smart TV in Each Bedroom | Sunroom | Access to Community Amenities | Golf Cart (Waiver May Be Required Prior to Use) Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Additional Sleeping: Queen Air Mattress COMMUNITY AMENITIES: Indoor & outdoor pools, hot tubs, basketball, racquetball, pickleball & tennis courts, golf course, music lessons, Zumba classes, yoga classes, game room, business center, bocce ball & shuffleboard courts, recreation center OUTDOOR LIVING: Private patio w/ gas grill (propane provided) & dining area, fenced backyard INDOOR LIVING: 4 Smart TVs, dining table, desk, 1,200 sq ft KITCHEN: Dishwasher, fridge, oven, 4-burner stovetop, microwave, breakfast bar w/ seating, drip coffee maker, tea kettle, toaster, toaster oven, cooking basics, dishware & flatware GENERAL: Free WiFi, keyless entry, central heating & A/C, ceiling fans, washer/dryer, linens/towels, complimentary toiletries, trash bags/paper towels FAQ: 2 exterior security cameras (facing out), pet fee (paid pre-trip), gated community ACCESSIBILITY: Single-story house, step-free access PARKING: Driveway (2 vehicles), garage (1 vehicle), guest parking area (1 vehicle, first-come, first-serve) -- THE LOCATION -- GOLF & RECREATION: Cane Garden Country Club (2 miles), Palmer Legends Country Club (4 miles), Churchill Street Recreation Center (6 miles), Pimlico Recreation Center (6 miles), Hawkes Bay Executive Golf Course (6 miles) THE GREAT OUTDOORS: Gazebo at Lake Sumter Landing in The Villages (4 miles), Sharon Rose Wiechens Preserve (6 miles), Paradise Park (8 miles), Heritage Park (8 miles), Bourlay Historic Nature Park (12 miles), Flat Island Preserve (15 miles), Sunnyhills Restoration Area (18 miles), Carney Island Recreation & Conservation Area (19 miles), Florida Horse Park (22 miles) LAKES: Lake Sumter Landing (4 miles), Lake Miona (5 miles), Grass Pond (5 miles), Lake Okahumpka Park (6 miles), Paradise Lake (8 miles), Lake Sunshine (8 miles), Lake Griffin State Park (8 miles), Tigerhead Lake (15 miles) HOT SPOTS: Brownwood Paddock Square Lady Lake Historical Society & Museum (5 miles), The Mammoth Live Oak Tree (8 miles), Paquette’s Historical Farmall Museum (10 miles), Leesburg Historical Museum (12 miles), Venetian Gardens (12 miles), Walt Disney World (54 miles), Gatorland (64 miles), The Baker House (86 miles) AIRPORT: Orlando International Airport (65 miles) -- REST EASY WITH US -- Property Manager 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 - Dog friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) - 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 at check-in - NOTE: This single-story home offers step-free entry - NOTE: If you wish to use the golf cart, please reach out to the Guest Contact prior to arrival - NOTE: This property sleeps 4 guests in 2 beds, with room for 6 total by using the queen air mattress - NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is a Ring doorbell device with an exterior security camera facing the front outdoor entry. Camera 2 is at the back of the property, facing the patio. The cameras face outward and do not look into interior spaces. The cameras record video and sound when activated by motion. Camera 2 is turned off when guests are in residence Licence number: DWE7000605;70-8019301405-2;70-8019301405-2;DWE7000605;70-8019301405-2;DWE7000605

Thurmond Retreat at Liberty Park in The Villages

The Villages, FL, US
2 Bedrooms 4 Guests
Sep 21 - 26
$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 Villages Home on Golf Course Near Lake Sumter!

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 24
$205 night

Soak up the best of the Sunshine State at this vacation rental! This 3-bed, 2-bath villa will feel like something out of a Florida portrait - framed by a white picket fence, swaying palm trees, and a yard overlooking the fairways. Stay close to home and enjoy on-site amenities—including a private golf cart and community pool—or wine and dine your way through Lake Sumter Landing 2 miles away. No matter how you spend your time, you'll feel refreshed, relaxed, and ready to call The Villages home! -- THE PROPERTY -- Complimentary Golf Cart | Pets Allowed | Community Amenities Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Twin Daybed w/ Twin Trundle Bed LARGO COMMUNITY: Neighborhood pool, clubhouse, postal station, Bacall recreation center, Bacall executive golf course OUTDOOR LIVING: Private backyard, 2 Adirondack chairs, mini putting green, screened-in patio w/ seating, golf cart INDOOR LIVING: Open floor plan, 3 flat-screen TVs, office desk, free WiFi, 4-person dining table KITCHEN: Fully equipped w/ stainless steel appliances, dishwasher, coffee maker, 4-person breakfast bar GENERAL: In-unit washer/dryer, linens/towels, air conditioning FAQ: Doorbell camera (facing front entry) PARKING: Garage (1 vehicle), driveway (2 vehicles) -- THE LOCATION -- LAKE SUMTER LANDING (2.2 miles): Old Mill Playhouse, Lighthouse Point Bar, RJ Gator's Florida Sea Grill, waterfront dining, shops, art galleries, entertainment ADDTL TOWN SQUARES: Brownwood Paddock Square (5.2 miles), Spanish Springs Town Square (5.0 miles), Lake Sumter Landing (2.2 miles), entertainment nightly from 5 to 9 PM GOLF COURSES: Bacall Executive Golf Course (on site), Hacienda Hills Country Club (5.1 miles), Pelican & Heron Golf Courses (2.5 miles), Havana Golf & Country Club (1.6 miles), Mallory Hill Country Club (1.2 miles) LAKES/PARKS: Lake Sumter (2.2 miles), Lake Griffin State Park (6.4 miles), Emeralda Marsh Conservation Area (20.9 miles) FAMILY FUN: Wilkerson Creek Park & Playground (1.8 miles), Uncle Donald's Farm (8.3 miles), GatorWorld (11.2 miles) DAY TRIPS: Orlando (57.3 miles), Walt Disney World (59.6 miles), Universal Studios (56.9 miles), Ocala National Forest (20.3 miles), Tampa (81.5 miles), Daytona Beach (75.0 miles) AIRPORT: Orlando Sanford International Airport (55.1 miles), Orlando International Airport (66.8 miles), Tampa International Airport (88.4 miles) -- REST EASY WITH US -- Property Manager 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 with $75 fee (+ fees & taxes) - 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: Your safety matters. This property features a doorbell camera on the front door facing the exterior front entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected or when the video doorbell button is pressed

1 Mi to Lake Sumter! Family Retreat w/ Large Patio

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 26 - 28
$187 night

Located in The Village of Virginia Trace, this palm-lined paradise offers easy access to many of Florida's wonders! Enjoy a prime location within an eight-minute walk of Downtown Lake Sumter Landing. Soak up theradiant sun while golfing, hiking, swimming, shopping, dining, and tuning into live performances. Book your next getaway now! -- THE PROPERTY -- Inside, memorable moments of family time are curated in the open-concept living room, dining area, and kitchen. Cuddle up on the oversized sofa while streaming your favorite TV shows and movies, or show off your culinary skills in the full kitchen. Cooking is made a breeze among the ample meal prep space and stainless steel appliances! Dining is just as easy at the breakfast bar, nook, formal dining table, or alfresco on the furnished lanai. Indulge in yourself as you enter the walk-in shower off the primary bedroom. Or, sink onto the plush bedding in each bedroom for a restful nap. With tasteful decorations, high-quality linens, and central air-conditioning in each of the bedrooms, there will be no arguments over room selection. The additional seating room is perfect for the kid's weekend morning cartoons and movie nights. And the adults will enjoy the separate bar where fruity cocktails can be made up and enjoyed. A private washer/dryer and designated work desk round out the home's interior perks. A block away, indulge in invigorating dips at the community pool, or kick back and enjoy the home's enclosed yard, extended lanai, grill, pizza oven, and firepit. -- THE LOCATION -- -- REST EASY WITH US -- Property Manager 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/ $200 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM to 8:00 AM - Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed Licence number: DWE7000582

Allenwood Pool Home at The Villages

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 26
$192 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.

High Point Getaway near Lake Sumter

The Villages, FL, US
3 Bedrooms 6 Guests
Sep 21 - 26
$113 night

✨ High Point Getaway near Lake Sumter ✨ This beautifully appointed home in the Village of Bonnybrook offers comfort, convenience, and full access to all The Villages has to offer. With three spacious bedrooms, a relaxing lanai, and a golf cart included, it’s the perfect spot for your Florida getaway. 🛏 Bedrooms & Layout Master Suite: King bed, flat-screen TV, large closet, and ensuite bathroom for privacy and comfort. Second Bedroom: A queen bed. Third Bedroom: A queen sofa bed. 🛋 Living Spaces Living Room: Comfortable seating, large flat-screen TV, and an open layout perfect for relaxing after a day of golf, swimming, or exploring. Dining Area: Spacious table for family dinners or morning coffee chats. Lanai: Outdoor seating area designed for al fresco dining, playing board games, or card nights. 🍳 Kitchen & Amenities Fully equipped kitchen: All essentials for home-cooked meals — cookware, dishes, utensils, coffee maker, toaster, microwave, and more. Laundry: Washer and dryer provided for your convenience. 4-Seater Golf Cart: Cruise to pools, recreation centers, squares, and shopping in true Villages style. 🌴 Location Highlights – Village of Bonnybrook Community Pool: Just steps away — right behind the house, past the bushes in the back. Ashland Pool & Recreation Center: Features a family pool, bocce, shuffleboard, pickleball, tennis, and billiards. Golf: Minutes to Arnold Palmer Country Club, Mallory Hill Country Club, and numerous executive courses. Ashland’s location gives you quick access to 40+ executive courses with your Villages ID. Lake Sumter Landing: Only a short golf cart ride away — enjoy nightly live music, waterfront dining, boutique shopping, and movies. Spanish Springs Square: Another square nearby with live entertainment, restaurants, and events. Recreation: Easy access to Coconut Cove Recreation Center, Lake Miona Regional Recreation Center, and walking trails. 🆔 Guest IDs & Access With your Temporary Resident ID ($50 paid directly to The Villages), you’ll enjoy access to: 40+ executive golf courses (free with ID) Championship golf courses (small fee applies) All community pools and regional recreation centers Pickleball, tennis, bocce, shuffleboard, and more Nightly live entertainment at all three squares 🌟 Why Guests Love This Home Two King bedrooms for ultimate comfort TVs in the living room and master bedroom Relaxing outdoor lanai with dining & games area Community pool right behind the home — just a few steps away Golf cart included for easy access to The Villages lifestyle

The Villages 2BR Vacation Home, Lanai & Golf Cart

The Villages, FL, US
2 Bedrooms 4 Guests
Sep 21 - 24
$108 night

Bright & Cozy Getaway | Golf Cart Included | Countless Community Perks Experience the ultimate Florida getaway at this bright 2-bedroom, 2-bath vacation rental in The Villages! Perfect for small groups or families, this home offers complimentary golf cart access to explore world-class community amenities, golf courses, and town squares. Relax in your private screened-in lanai, fire up the patio grill after a day at the beach, or unwind in the cozy living area. Book your sunny retreat today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Additional Sleeping: 1 queen air mattress COMMUNITY AMENITIES (w/ fee, paid on-site) - 83 heated saltwater pools - 38 golf courses, 12 championship golf courses - Clubhouses, basketball court, racquetball, bocci ball - Horseshoes, community fitness center, recreation center - Rumba, poker & bridge, shuttle OUTDOOR LIVING - Screened-in porch - Outdoor seating & dining - Patio - 4-seater golf cart INDOOR LIVING - Flat-screen TVs (streaming services only, no cable) - Fireplace, 2 dining tables - Walk-in shower, shower/tub combo - Ceiling fans KITCHEN - Stove/oven, refrigerator, dishwasher - Cooking basics, dishware/flatware - Coffee maker, Crockpot, ice maker - Microwave, toaster, water filter, spices GENERAL - Gated community - Free WiFi - Central heating & air conditioning - Complimentary toiletries, hair dryer - Washer/dryer (garage), laundry detergent - Linens/towels, beach towels - Trash bags/paper towels ACCESSIBILITY - Step-free access, single-story home FAQ - Quiet hours (10:00 PM-8:00 AM) - Pet fee (paid pre-trip) - 2 external security cameras (facing out) PARKING - Garage (1 vehicle), driveway (1 vehicle) -- THE LOCATION -- - Located in The Villages with access to extensive community amenities, including over 30 golf courses (passes are $50 for 2 people), 100+ recreation centers with pools, fitness centers, pickleball, tennis, parks & arts facilities. 3 town squares offer shopping, dining & free nightly live entertainment - 4 miles to Sunset Park - 11 miles to Lake Griffin State Park - 12 miles to Eatons Beach - 13 miles to Kayaking Florida Waters - 61 miles to Walt Disney World Resort - 30 miles to Ocala International Airport & 84 miles to Orlando Sanford International Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes, 2 pets max) - No events, parties, or large gatherings - Must be at least 55 years old to book - Please observe quiet hours from 10:00 PM to 8:00 AM - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - In order to access the community amenities, guests must pay a required fee of $50 to obtain a guest access card - Your safety matters. This property features 2 exterior security cameras. Camera 1 is located on the front exterior, facing outward toward the driveway, and camera 2 is on the side patio facing the side lawn. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion. The cameras will record when they first sense motion and 30 seconds after the last motion is detected Licence number: 88-4068818

Twisted Oak House

The Villages, FL, US
3 Bedrooms 6 Guests
Dec 5 - 7
$118 night

IMPORTANT !!! JAN & FEB require to be booked together / no partial bookings allowed Turtle Haven House 🐢🏡 Welcome to Turtle Haven House, a charming designer model home located on a desirable corner lot in the heart of The Villages, FL. This beautifully decorated three-bedroom, two-bath residence in the Village of Sanibel is your perfect retreat, combining luxury, comfort, and a playful turtle-themed ambiance throughout. Coastal Charm with Modern Comfort Turtle Haven House offers a cozy and welcoming atmosphere with quality furnishings and tasteful decor. The open-concept living area features sliding doors that seamlessly extend your living space to a relaxing screened-in private lanai. This outdoor oasis is ideal for entertaining or enjoying your morning coffee while soaking in the Florida sunshine. Work and Play in Style The third bedroom is thoughtfully designed as an office, perfect for those who need a quiet space for remote work or creative pursuits. With fast Wi-Fi and a comfortable desk setup, balancing work and leisure has never been easier. Location, Location, Location Located just minutes away from Lake Sumter Landing and Brownwood Paddock Square, you’ll have easy access to some of the best dining, shopping, and entertainment in The Villages. Take a leisurely stroll to the Sanibel Recreation Center or tee off at the nearby Bonifay Country Club. Whether you prefer championship or executive golf courses, this prime location puts you in the middle of it all. Explore The Villages With over 40 executive golf courses and numerous championship courses just around the corner, golf lovers will be in paradise. Enjoy hundreds of activities, from pickleball and tennis to arts and crafts workshops, fitness classes, and more. Plus, there’s live music every night at the town squares, making it easy to find fun and excitement any day of the week. Live the Villages Lifestyle Take advantage of the included gas-powered, two-seat golf cart for quick and easy access to everything The Villages has to offer. With a variety of outdoor activities, shopping centers, medical facilities, and dining options all within a short ride, you’ll never run out of things to do or explore. Make Your Move Experience the best of Florida living at Turtle Haven House. With its prime location, luxurious features, and vibrant community, this home is perfect for those looking to embrace a lifestyle full of adventure, relaxation, and fun. Contact us today to book your stay and start making unforgettable memories in The Villages!

Golf Cart & Amenity Access! Home in The Villages

Wildwood, FL, US
3 Bedrooms 6 Guests
Sep 21 - 23
$150 night

Fenced-In Backyard | Retirement Community | Located in The Villages | EV Charger Experience all that The Villages has to offer with a stay at this 3-bedroom, 2-bath vacation rental in Wildwood. This well-appointed home offers a spacious lanai, a fenced-in yard for your furry friends, and a prime location a golf cart ride away from Red Fox and Gray Fox Executive Golf Course. Enjoy access to community amenities including golf and pickleball, plus nightly live entertainment at Sawgrass Grove! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 sleeper sofa COMMUNITY AMENITIES (resident IDs for access are provided) - Pool, hot tub - Recreation center, pickleball courts INDOOR LIVING - Smart TVs - Dining table - Ceiling fans - Books, office space KITCHEN - Dishwasher, microwave - Cooking utensils, dishware & flatware - Blender, coffee maker, ice maker, spices, toaster OUTDOOR LIVING - Screened-in patio w/ seating - Golf cart - Bicycles GENERAL - Free WiFi - In-unit laundry machines, iron/board - Central air conditioning - Complimentary toiletries, hair dryers, hangers - Keyless entry, linens/towels, trash bags/paper towels FAQ - Pet fee (paid pre-trip) ACCESSIBILITY - Single-story home, step-free access PARKING - Driveway (2 vehicles) - Garage (1 vehicle) - Free street parking - EV charger available -- THE LOCATION -- - Less than a mile to Fenney Recreation Center & Pool - 0.4 miles to Red Fox and Gray Fox Executive Golf Course - 3 miles to Magnolia Shopping Plaza - 7 miles to Lake Okahumpka Park & 8 miles to Sharon Rose Wiechens Preserve - 53 miles to Universal Studios, Walt Disney World Resort, Epcot, Madam Tussauds Orlando - 62 miles to Orlando International Airport -- REST EASY WITH US -- Property Manager 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, max 2 pets) - 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

Timber Sunshine Stay (Villages of Dunedin)

The Villages, FL, US
3 Bedrooms 6 Guests
Oct 2 - 9
$107 night

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

Vacation Rentals in Wildwood by Amenities & Features

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Vacation Rentals Near Wildwood

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