
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.

Ibis Cove-Waterfront townhouse with great reviews!
Ibis Cove is a peaceful bit of real Florida on the quiet side of our quaint little neighborhood. Our canal leads to the Tsala Apopka Chain of Lakes. Use our canoe and kayak to enjoy 22,000 acres of connecting lakes. Bring your bikes and enjoy easy access to 46 miles of a great bike trail. Inside, enjoy a spotlessly clean and beautifully decorated townhouse with all the conveniences of home. Porch and balcony give access to a Florida landscape of water, Cypress trees and assortment of wildlife.

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.

Whole House-sleeps 10 The Villages Spanish Springs
Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

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.

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.

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.

Safari themed private addition with pool/hot tub.
This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

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.

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.

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. I offer a golf cart 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!

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

Briar Meadow Villa - Dogs are welcome!
Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart, Comcast cable TV, high speed WIFI, & Villages Daily Sun.
Popular amenities for Wildwood rentals with a pool
House rentals with a pool

Village of Deluna at Marsh Bend 3bd 2bth

Relaxing House in The Villages

Walk to Sawgrass! Near Eastport | Golfcart | Patio

The Villages, Heated Pool Walk to Sawgrass

Willie’s Place w/Golf Cart, Hot Tub & Dog Friendly

Entire House in The Villages

Robin's Song in Brownwood

The Villages, Citrus Grove home away from home
Condo rentals with a pool

Welcome In! Epic/OCCC/Shingle 1-floor

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Westgate Palace Resort 2 bedroom

Resort Condo: 2BR w/ Balcony near Disney

VISTA CAY RESORT, 3 BEDROOM STANDARD APARTMENT

No Airbnb Fees! Universal 1.9 miles away! 1401

Lakefront Studio •Private Terrace• near Universal

Vista Cay Poolside Diamond, Next to EPIC and OCCC
Other vacation rentals with a pool

Beautiful 3BR Ocala Home | Perfect for Families

PATIO VILLA W/GOLF CART 1M TO SQ-NO XTRA GUEST FEE

On The Links-4bd w/pool in Spanish Springs!

Home with private pool, Tierra grande villas

Charming Villages Retreat

Eden Escape Suite, Lake Harris, Florida

Gator Palms - large house with view of pond

Villager luxury-Minutes to Brownwood or Eastport!
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 657 | ﺩ.ﺇ 746 | ﺩ.ﺇ 735 | ﺩ.ﺇ 477 | ﺩ.ﺇ 455 | ﺩ.ﺇ 437 | ﺩ.ﺇ 411 | ﺩ.ﺇ 404 | ﺩ.ﺇ 408 | ﺩ.ﺇ 433 | ﺩ.ﺇ 492 | ﺩ.ﺇ 536 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
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 ﺩ.ﺇ 147 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!
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- Universal Studios Florida
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- Orange County Convention Center
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- Magic Kingdom Park
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- Reunion Resort Golf Courses - Palmer & Watson
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- ChampionsGate Golf Club
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