
Vacation rentals with a pool in The Villages
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in The Villages

Total vacation rentals
Explore 340 vacation rentals in The Villages

Nightly prices starting at
The Villages vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 8,140 verified reviews to help you choose

Family-friendly vacation rentals
310 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
340 of The Villages vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across The Villages rentals

4.9 Average rating
The Villages stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in The Villages
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

Sunset Oasis - 3/2 w/ Pool & Golf Cart
Breathtaking! This 3BR 2BA w/ POOL and GOLF CART, in the Village of Lake Denham, will leave you speechless! Not only is paradise inside the house, but you have an amazing waterfront view while you revel in the private pool. Comfortable beds, open floor plan, it's stunning! Cruise around on the golf cart to discover rec. centers, pools, golf courses for all level of players, and pickleball courts. The squares certainly won't disappoint with their restaurants, shopping and nightly live music.

Heated Pool Golf Cart Dog Friendly in The Villages
Nestled amidst lush greenery ,Vida Rosa’s private pool provides a serene outdoor oasis, complete with a dining area, loungers, and a gas BBQ. The luxurious accommodations are thoughtfully designed to evoke a sense of calm and elegance. Conveniently located, just a short golf cart ride away from the squares of Spanish Springs & Lake Sumter offering a variety of entertainment etc. Note: The pool has a jet tub attached to it. The water temperature is the same temperature as the pool, 86 .

Pool, golf cart, private backyard. Paradise!
Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

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!

Pirates & Parrots - The Villages - w/Golf Car !
GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

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.

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!

King Bed, Small Dogs OK, and 4-Seater Golf Cart!
Your NEW home includes a very comfortable KING BED. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house 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!!
Popular amenities for The Villages rentals with a pool
House rentals with a pool

Pool Home Great Location 3/2 & 2 Golf Carts

Beautiful Designer Home in The Villages Fl

Designer Home in The Villages, FL.

Home with private pool, Tierra grande villas

New, private pool getaway in The Villages, FL

Serenity - In The Villages

A patio villa in Deluna, The Villages w/ Golf Cart

Robin's Song in Brownwood
Condo rentals with a pool

20 Mi to Disney: Condo w/ Pool Access in Clermont!

1 Bedroom 5-Star Standard Resort Villa Near Disney

Wafflemaker Waterfront condo 2BR full ensuite pool

Cypress Cove Waterfront Townhome

Beautifal 2 Bedroom 5-Star Grand Villa

1 Bedroom 5-star Grand Resort Villa Near Disney
Other vacation rentals with a pool

Casa Bella: 3 Bedroom 2 Bath House Sleeps 6

Villa la Bella

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

5-Star Luxury | Prime Location & Top Amenities

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

Slice of Paradise! Great location in The Villages!

House on Golf Course, with Heated Pool & Golf Cart

Entire House in The Villages
When is the best time to visit The Villages?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ639 | ﺩ.ﺇ679 | ﺩ.ﺇ661 | ﺩ.ﺇ474 | ﺩ.ﺇ452 | ﺩ.ﺇ433 | ﺩ.ﺇ386 | ﺩ.ﺇ375 | ﺩ.ﺇ422 | ﺩ.ﺇ433 | ﺩ.ﺇ499 | ﺩ.ﺇ521 |
| 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 |
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Orange County Convention Center
- 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
- Weeki Wachee Springs
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Rainbow Springs State Park
- Universal's Islands of Adventure
- Shingle Creek Golf Club
- Ocala National Forest




