
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.

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.

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!

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

Fenney Waterview Retreat w/Pool in The Villages
If you are looking for a Tranquil escape, then this is the right home for you. Sit by the pool and overlook the sun dance upon the sparkling water as you sip on your drink or read a great book. This Ultra Clean 3 bed/3 bath home has all of the comforts you'll be looking for. There's plenty of space for you and friends or family as everyone has their own space in the home.
Popular amenities for Wildwood rentals with a pool
House rentals with a pool

Casa Bella: 3 Bedroom 2 Bath House Sleeps 6

Villa la Bella

Lake Dora Dream-Waterfront/Pool

Villages-Waterfrnt, 3 king bds/2.5Ba+golf crt

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

Village of Deluna at Marsh Bend 3bd 2bth

Walk to Sawgrass! Near Eastport | Golfcart | Patio

Willie’s Place w/Golf Cart, Hot Tub & Dog Friendly
Condo rentals with a pool

Vista Cay Luxury Vision, Next to EPIC and OCCC

Penthouse Lakeview Minutes to Disney/ Universal

Disney Area Updated Lakefront Resort Condo 2 POOLS

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

Crystal River Bungalow with boat slip

Waterfront Condo minutes to Disney & Universal

Modern Lake view Condo 1 mile from Disney

Renovated Condo 2 miles away from Disney Lake view
Other vacation rentals with a pool

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

5-Star Luxury | Prime Location & Top Amenities

Heated Pool Golf Cart Dog Friendly in The Villages

Home with private pool, Tierra grande villas

Charming Villages Retreat

Eden Escape Suite, Lake Harris, Florida

Sea Horse House

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 | G$37,420 GYD | G$42,437 GYD | G$41,810 GYD | G$27,177 GYD | G$25,922 GYD | G$24,877 GYD | G$23,414 GYD | G$22,996 GYD | G$23,205 GYD | G$24,668 GYD | G$28,013 GYD | G$30,521 GYD |
| 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 G$8,362 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!
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Weeki Wachee Springs
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Rainbow Springs State Park
- ChampionsGate Golf Club
- ESPN Wide World of Sports





