
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 330 vacation rentals in The Villages

Nightly prices starting at
The Villages vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 8,210 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wi-Fi availability
330 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.

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.

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.

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.

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 - Golf Cart &Pool
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.

Hot Tub Hideaway | Golf Cart | The Villages
Your home in The Villages comes with something most don't — a private in-ground hot tub on a screened lanai, an outdoor kitchen with a pizza oven, and your own golf cart. This beautifully renovated 2-bed, 2-bath home pairs an open-concept layout with a white-shaker chef's kitchen, hardwood floors, and a king primary suite. We arrange your Lifestyle IDs ($50) before arrival so they're ready for you to pick them at the sales office. This home is 100% within The Villages community.

King Bed, Golf Cart, Small Dogs & Water Filter!
Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA 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!! 2 SMALL DOGS OK.

Heated Pool + GOLF CART - Village of Santiago!
So much to love! This POOL home with GOLF CART provides a tranquil and comfortable get-a-way for you visit to THE VILLAGES. All the essentials are provided. 3.5 miles from Spanish Springs 5.5 miles from Lake Sumter Landing .9 miles to the Savannah Center 1.3 miles to Glenview Country Club. & Golf Course Close to many recreation centers, golfing, & shopping. On a nice quiet cul-de-sac! Small dogs under 20 lbs permitted with pet fee.

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

Stylish Villages Getaway
Welcome to your modern luxury escape in The Villages. Perfect for snowbirds, couples, or families, this brand-new home is designed for comfort and convenience. Enjoy high-end furnishings, elegant interiors, and access to resort-style community amenities. Make the most of your stay with a premium 6-passenger golf cart, electric bikes, and endless entertainment. Stay active, relax, and create unforgettable memories.
Popular amenities for The Villages rentals with a pool
House rentals with a pool

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages

Cozy Lady Lake Guest House

Casa Santin Luxury in The Villages w/Private Pool

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

StJohns is a great area for golf, hiking, Kayaking

Eastport Emerald Escape 2BR Luxury in Well Point

The Sunseekers Eco-Villa

Charming Villages Retreat
Other vacation rentals with a pool

Heated Pool Golf Cart Dog Friendly in The Villages

Perfect location Lake Sumpter Villa w/ Golf Cart

Pool and Spa Luxury Retreat

Holiday home in the villages.

Incredi-Bill Jo's

Villages home with unique elevated front porch

CLEAN! Walk to pools; Golf Cart; NO Xtra guest fee

Living the Dream | Pools, Golf & Entertainment
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.ﺇ 654 | ﺩ.ﺇ 716 | ﺩ.ﺇ 727 | ﺩ.ﺇ 547 | ﺩ.ﺇ 459 | ﺩ.ﺇ 441 | ﺩ.ﺇ 386 | ﺩ.ﺇ 375 | ﺩ.ﺇ 422 | ﺩ.ﺇ 433 | ﺩ.ﺇ 499 | ﺩ.ﺇ 521 |
| 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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