Vacation rentals with a pool in Wildwood

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wildwood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Lady Lake

4.96 out of 5 average rating, 313 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Top guest favorite

Home in The Villages

5 out of 5 average rating, 15 reviews

Entire Home with an Office in Fenney

My home is furnished for the ultimate in guest comfort and working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, printer, TV Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days, ask for details

Top guest favorite

Home in The Villages

5 out of 5 average rating, 78 reviews

Calming Pool Oasis in Fenney, The Villiages FL

Enjoy your Very Own Private Pool Getaway in this gorgeous home in The Village of Fenney. Wake up relaxed with your morning coffee in hand sitting on the screened in lanai. Cleanliness is our #1 priority for you to have a worry free stay. Vaulted ceilings, Ceiling Fans, State of the Art Stainless appliances make this property an oasis away from stress. Watch your favorites on 1 of 5 Flatscreen TV's. If you are looking for your home away from home for 1 night or 90 nights, this is "the" place

Top guest favorite

Home in Wildwood

5 out of 5 average rating, 17 reviews

Brownwood Square - Villages Home

Indulge in a stylish retreat at this centrally located home, just minutes from the vibrant Brownwood Square in the sought-after Village of DeLuna. Immerse yourself in the full Villages experience with a community pool, recreation center, and included golf cart—perfect for exploring. Enjoy nearby shopping, dining, live music, nightlife, sports, and more. Explore Central Florida or take a short drive to the Gulf Coast, Atlantic Ocean, Disney, or Orlando’s vibrant attractions—all within an hour!

Top guest favorite

Home in The Villages

5 out of 5 average rating, 12 reviews

The Villages, Citrus Grove home away from home

Create great memories at this centrally-located home, with an open floor plan with vaulted ceilings. The kitchen is well equipped and the living room has a queen size sleeper sofa and a smart TV (internet/WIFI). The master bedroom has a king size bed, walk in closet, smart TV, master bathroom and a work area with a desk and printer. The guest bedroom has a queen size bed, large closet and smart TV. Both bedrooms have black out curtains and hair dryers, and linens. Grill/2 bikes incl.

Top guest favorite

Home in The Villages

4.96 out of 5 average rating, 84 reviews

Private Pool with Sunset View in Monarch Grove

New home. In new village. Western sun exposure for your afternoons by the pool. Rest, relax, and enjoy your lifestyle in THE VILLAGES. Over 3000 clubs of activities, 30+ golf courses and country clubs 20+ public pools, plus your own private pool. 3 downtown squares of live entertainment 365 days a year. 40 minutes to DisneyWorld, Universal Studios, Orlando Florida. Everglades recreation center is 1 mile away and has 50 acres of outdoor activities. 21 miles of walking, biking trails.

Top guest favorite

Home in The Villages

4.99 out of 5 average rating, 73 reviews

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

Top guest favorite

Home in The Villages

5 out of 5 average rating, 15 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

Enjoy this beautiful 2/2 home in De Luna. With quick access to the turnpike and I-75 to enjoy everything in and around the Villages. This Ruby model villa is close to Brownwood and Ednas’ on the Green & soon to be East Port. It comfortably fit 4 people in two queen beds. The living room can fit two on the pull out sectional. The front screen porch is a wonderful place to wave to your neighbors while you have your morning coffee or just the place to relax before going to bed.

Top guest favorite

Home in The Villages

4.93 out of 5 average rating, 15 reviews

The Grandview

Sure to wow and impress you, this stunning premier home has it all. With four spacious bedrooms, you can bring the whole family for some memories and fun. A sparkling pool and an inground hot tub await you on the sprawling lanai, complete with ample seating and an outdoor kitchen. This home is just minutes from Lake Sumter Landing and all the shopping, dining, golf, recreation and activities you could imagine! Golf cart for your convenience. Golf cart is not guaranteed.

Superhost

Home in Wildwood

5 out of 5 average rating, 4 reviews

Pool and Spa Luxury Retreat

Escape to this charming 3BR/2BA home in The Villages, FL! Enjoy a private heated pool & spa, perfect for relaxation. Walk to the nearby recreation center or take a short 1-mile ride to Eastport. This home includes a 4-person golf cart, making it easy to explore all The Villages has to offer. Comfortably furnished with modern amenities, it’s ideal for a peaceful retreat or an active getaway. Book now for the perfect blend of convenience and leisure!

Top guest favorite

Home in The Villages

4.95 out of 5 average rating, 126 reviews

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Top guest favorite

Home in Wildwood

4.93 out of 5 average rating, 15 reviews

The Villages - Sunshine and pickleball

Golf Cart included! Bring the whole family to this lovely 2024, 4BR, 2 bath home close to Brownwood Center with lots to do and plenty of room for all! Enjoy Pickleball, tennis, golf, swimming, hiking, biking, plenty of outdoor activities, and nightly music venues. Free Guest passes available upon request for amenities. Always something happening, for people of all ages. There’s nothing like The Villages!