
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.

2/2 custom pool home with 4 person gas golf cart
Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

Entire Home with an Office in Fenney
Furnished for the ultimate in guest comfort, entertainment & working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, TV, printer 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

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.

Silver Lake Guest Pool House Very Private !
The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

King-Sized Comfort
Take a break and unwind at this peaceful oasis.Welcome to your serene getaway in The Villages! This spacious “Hideaway” in peaceful DeLuna offers 2 king beds, 2 baths, and easy access to pools, pickleball, tennis, and more. Explore over 130 miles of golf cart paths in this vibrant 55+ community featuring 700+ golf holes, 100+ pools, and endless clubs and activities. Just an hour from Orlando’s theme parks and near cruise ports, it’s the perfect mix of fun, comfort, and Florida sunshine!

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.

Patio Villa - Pet Friendly 2/2 Home (South of 44)
**January - March Rentals are Minimum of 30 Days** This is a beautiful FULLY FURNISHED, 2/2 Patio Villa Home in the Villages, Florida . There is a spacious comfy living room with lots of seating as well as TV (cable/wifi) We now offer Golf Cart Rentals for additional fee. (2 Passenger $35/day, $175/week) (4 Passenger $55/day, $275/week) PETS: 2 Small dogs, $75.00. non refund/pet; sec dep will be used for any pet damages; renter liable for entire cost of damage VILLAGE IDs- $25/ea

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!

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.

A-Frame Cottage near Disney, Universal, & Lakes
Come enjoy a relaxing stay at the Dragonfly Cottage and explore all that Central Florida has to offer. With Disney World just 23 miles (37 km) and Universal Studios 26 miles (42km) away, you will find plenty of entertainment. Beautiful Lake Louisa State Park is less than 3 miles (5 km) and the Downtown Clermont Lakes only 6 miles (9 km) away. With amenities like an Olympic-size pool just steps away, you'll be able to cool off and unwind after long days of sun and fun.

New home in the new part of the villages.
Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.
Popular amenities for Wildwood rentals with a pool
House rentals with a pool

5-Star Luxury | Prime Location & Top Amenities

The Villages, De La Vista West 1762

Spotless Villa Near Brownwood Sq- Lanai & King Ste

Waterfront, Heated Pool, Golf Cart, & 2 King Beds

Welcome to the Villages

Slice of Paradise! Great location in The Villages!

Gem in the Villages! Free golf cart with waiver

Charming Villages Retreat
Condo rentals with a pool

Beautiful Beach Style Condo minutes from Disney

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️

Disney Oasis by the lake

Private Rooftop Suite! No resort fees!

The Point Hotel & Suites - 705H Luxury - Pool View

Modern Lake view Condo 1 mile from Disney

Stunning view, near Disney.
Other holiday rentals with a pool

The Villages 4 Golf, PickleBall & a whole lot more

The Palms. Luxurious, giant pool, golf, pond view

Villages home with unique elevated front porch

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

Relaxing House in The Villages

Heated Pool Golf Cart Dog Friendly in The Villages

Sunset Oasis - 3/2 w/ Pool & Golf Cart

Lazy Day Getaway*New Const*2bd/2ba*Pet Friendly
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 AUD | $248 AUD | $245 AUD | $184 AUD | $176 AUD | $169 AUD | $159 AUD | $156 AUD | $157 AUD | $167 AUD | $190 AUD | $207 AUD |
| 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 $57 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 160 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
430 of Wildwood holiday 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
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- 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
- Aquatica
- Disney's Hollywood Studios
- Camping World Stadium
- ICON Park
- Island H2O Live!
- ChampionsGate Golf Club
- Ocala National Forest
- Shingle Creek Golf Club




