Vacation rentals with a pool in Wildwood

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Wildwood

  • Total vacation rentals

    Explore 460 vacation rentals in Wildwood

  • Nightly prices starting at

    Wildwood vacation rentals start at G$8,359 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,820 verified reviews to help you choose

  • Family-friendly vacation rentals

    410 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wi-Fi availability

    460 of Wildwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wildwood rentals

  • 4.9 Average rating

    Wildwood stays are highly rated by guests—averaging 4.9 out of 5!

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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Guest favorite
The exterior of a spacious single-story house is visible, featuring a light-colored facade and a greenery-laden yard. A palm tree is seen in the foreground, while the driveway leads towards a garage on the right side.
Home in The Villages
4.92 out of 5 average rating, 146 reviews

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages

Live Music on the Square. Golf , Pools, tennis, etc Spacious 3 bedroom house in The Villages. The house has a hot tub on the back lanai. The house is newly renovated and features both a new 70 inch Samsung TV in the living room and a new 50 inch Samsung TV in the master bedroom with Hulu Live and Comcast Business high speed internet. The house is located near the Spanish Springs Town Center and Glenview Country Clubs. The home sleeps 8 with privacy using a sofa bed located in the rec room.

Top guest favorite
A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.
Home in Wildwood
4.97 out of 5 average rating, 35 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, 15 reviews

Pool House Near Eastport and Middleton

Relax at this peaceful new home in The Villages. Only minutes to Eastport ,Sawgrass and Middleton. Enjoy the beautiful outdoor area and heated pool (heated for additional $20/day) with plenty of space and seating. There are TVs in the living bedrooms and the lanai to watch from the pool or comfortable outdoor seating. There’s a king bed in the master and queens in each of the guest bedrooms. Your stay includes a gas 4 seater Yamaha golf cart and probably a 2nd cart. That one’s not promised.

Top guest favorite
An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.
Villa in The Villages
4.86 out of 5 average rating, 269 reviews

Perfect "get-away" home for a couple or family!

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

Top guest favorite
A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.
Home in Wildwood
4.97 out of 5 average rating, 89 reviews

Newer Villa in The Villages near Brownwood

Kick back and relax in this calm, stylish new villa in the Villages. It is within walking or a 3 minute golf cart ride to Brownwood Town Center where there are dining, shopping and nightly music. It is also near Lake Okahumpka Recreation Center where you can fish or kayak. This area has beautiful nature trails for walking or biking with separate golf cart paths. There is a neighborhood pool and other amenities nearby. It also comes with a complementary golf cart for your convenience.

Top guest favorite
Home in Wildwood
5 out of 5 average rating, 38 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

Guest favorite
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages
4.85 out of 5 average rating, 128 reviews

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

Top guest favorite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 104 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

Top guest favorite
Home in The Villages
4.96 out of 5 average rating, 96 reviews

King Bed, Golf Cart, Small Dogs & Water Filter!

Your NEW home includes a very comfortable KING BED and 4-Seater GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

Guest favorite
A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.
Home in Wildwood
4.9 out of 5 average rating, 94 reviews

New, private pool getaway in The Villages, FL

The whole group will enjoy easy access to everything from this centrally located 3B/3BA home in the village of St Catherine. Just steps away from Sawgrass marketplace where you can enjoy dinner, nightly entertainment, pickle ball, and golf at the brand new Southern Oaks 18 hole championship golf If staying in is your idea of relaxation, enjoy the oversized lanai and private heated pool while watching your favorite shows or sports on the 65" smart TV.

Top guest favorite
Home in Wildwood
5 out of 5 average rating, 9 reviews

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

Relax at Pleasantville, a newly furnished home in The Village of McClure! Golf cart included for easy trips to Sawgrass Grove, Brownwood Square, Magnolia Plaza, and top golf courses. Enjoy pools, pickleball, walking trails, and more at nearby rec centers. Just 5 mins from Eastport’s golf academy & Sunset Island. Quiet, scenic, and perfect for fun, relaxation, and adventure—only 1 hour from MCO and Disney parks!

Top guest favorite
Home in The Villages
5 out of 5 average rating, 15 reviews

Begonia on the Bend – Stylish Home Near Sawgrass

🌴 Modern 3BR/2BA Begonia-style home in The Villages’ new Cason Hammock neighborhood. Built in 2021, this spacious 2,083 sq ft retreat features an open layout, oversized garage + golf cart garage, and stylish comfort throughout. Walk to Sawgrass Town Square, McGrady’s Pub, pool, rec center, and Fresh Market. Enjoy The Villages lifestyle with everything you need for a relaxing stay!

Popular amenities for Wildwood rentals with a pool

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,409 GYDG$42,424 GYDG$41,797 GYDG$27,168 GYDG$25,914 GYDG$24,869 GYDG$23,406 GYDG$22,988 GYDG$23,197 GYDG$24,660 GYDG$28,004 GYDG$30,512 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Destinations to explore

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  2. United States
  3. Florida
  4. Sumter County
  5. Wildwood
  6. Rentals with pools