
Holiday 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.

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! Heating of the pool and spa included in rate.

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.

Walk to Sawgrass! Near Eastport | Golfcart | Patio
With a golf cart included, this home is a short walk to Sawgrass, with Eastport Sq. only 7 mins away. Brownwood Paddock & Middleton are both 11 minutes away, putting you close to great dining & shopping! Inside, you’ll find a spacious open layout with comfy furnishings, a fully equipped kitchen, & a relaxing patio with a griddle. The bedrooms are well furnished & include a dedicated work area & ensuite bathroom for comfort A $50 fee applies for the Lifestyle ID & golf cart insurance is $20

Poolside Paradise-w/ Pool & Golf Cart The Villages
Welcome to Poolside Paradise! Your dream getaway in a fantastic location within The Villages, FL. Nestled in The Village of Chitty Chatty, this stunning 4-bed, 3-bath retreat is your ticket to ultimate relaxation and fun. Explore the vibrant surroundings with ease, thanks to the complimentary 4-seater golf cart provided for your convenience. There are four (4) bikes available for guest use as well. You will have easy access to multiple recreation centers, town squares, & entertainment venues.

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.

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.

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.

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.

Serenity - In The Villages
Escape to this stunning Moonstone Home near Eastport Square, Publix, and Fenney Rec Center. Enjoy nature trails, pools, Fenney Grill, and executive golf, all easily reached by golf cart. Relax on the private lanai, cook in the chef’s kitchen, and enjoy stylish comfort in a peaceful setting. Catch SpaceX launches from the patio. Golf cart available for $25/day or $350/month.
Popular amenities for Wildwood rentals with a pool
House rentals with a pool

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

Relaxing House in The Villages

The Villages - Sunshine and pickleball

Dreaming of DeLuna

The Villages, Heated Pool Walk to Sawgrass

Charming Villages Retreat

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

Screened-In-Optional Heated Pool+Fence+Arcade +Bbq
Apartment rentals with a pool

Location,Location 3bd 2bth near parks conv.ct/Int.

Maria Luz Studio-Huge Terrace/Universal area.

Private Rooftop Suite! No resort fees!

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

Westgate Palace Resort 2 bedroom

Vista Cay 3 Bedrooms Theme Parks Convention Center

VC13-303 | Vista Cay 3BR Family Condo Near Disney

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT
Other holiday rentals with a pool

Villa la Bella

5-Star Luxury | Prime Location & Top Amenities

Villages - Priv. Htd. Pool 3BR/2BA, Conv. Location

Heated Pool Golf Cart Dog Friendly in The Villages

The Sunshine Retreat with Golf Car

My Haven Is Heaven

Entire House in The Villages

Villager Luxury Escape! Minutes to Brownwood!
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $222 SGD | $223 SGD | $221 SGD | $166 SGD | $158 SGD | $152 SGD | $143 SGD | $140 SGD | $141 SGD | $150 SGD | $171 SGD | $186 SGD |
| 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 holiday rentals with a pool in Wildwood

Total holiday rentals
Explore 430 holiday rentals in Wildwood

Nightly prices starting at
Wildwood holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 8,350 verified reviews to help you choose

Family-friendly holiday rentals
380 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
430 of Wildwood holiday rentals include wifi 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
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- Aquatica
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- ChampionsGate Golf Club
- Rainbow Springs State Park




