
Vacation rentals with a pool in The Villages
Find and book unique homes with a pool on Airbnb
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

Waterfront, Heated Pool, Golf Cart, & 2 King Beds
GET IT ALL - Pool, Golf Cart & Waterfront Located in the Village of Palo Alto, this vacation home is nestled on a quiet street and backs up to a lake. Newly renovated, it has 3 bedrooms and 2 baths, and updated furnishings. It features a sparkling private pool and spacious lanai area. It's centrally located between the town squares of Spanish Springs and Lake Sumter Landing. Your rejuvenating vacation awaits. Book it today! No cats. Dogs under 40 lbs allowed with pet fee. Gas grill available.

2/2 Villa 5 min from Lake Sumter Landing-pets
2 bed/2 Bath Villa,Pet fee,Golf Cart included,screened lanai,large patio. Nicely decorated, meticulously maintained. Perfectly centrally located 5 minutes by Golf Cart to the Sumter main entertainment Square & 20 min. from Brownwood Square. Close to Executive Courses, & Cane Garden and Mallory Champion courses. More to explore, all sports, Adult & Family Pools. Restaurants, shopping, nightly Live Musical Entertainment & so MUCH more! What are you waiting for? Book today and enjoy life.

The Coconut Courtyard-Private pool & Tiki Hot tub
Private Heated saltwater pool. A tiki hot tub to die for, modern spacious home. We have bedrooms themed after the town squares! Walk to the Lopez course/restaurant. We have one of the largest corner lots in The Villages. Outdoor seating, pool is screened in. Our kitchen is fully stocked for cooking, the home is spotless clean with little luxuries that will surprise you. We are half way between Spanish Springs and Lake Sumpter. Easy cart ride to eat, dance, shop, golf, & more! #memories

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.

Dreaming of DeLuna
Enjoy all The Villages has to offer in this beautiful, well stocked, roomy 2 bed / 2 bath Patio Villa nestled in the Village of DeLuna. Whether you are visiting family, escaping the cold, enjoying some needed R & R, or just checking out The Villages, you will feel at home in this wonderful Villa. Short golf cart ride to Magnolia Shopping Plaza, Brownwood Paddock Square and Eastport, Water Lilly and Everglades recreation centers, multiple pools, pickleball, tennis, and of course GOLF.

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

The Villages, De La Vista West 1762
* Just available, complete renovation/new everything of this Patio Villa. * Considered one of the best locations, right in between Lake Sumter Landing and Spanish Springs squares, close to main intersection of CR466 and Morse Blvd. * Over-sized lot on street end, no homes behind, mature trees and 3 outdoor entertaining areas. *January, February and March are only rented consecutively.
Popular amenities for The Villages rentals with a pool
House rentals with a pool

Villa la Bella

Begonia on the Bend – Stylish Home Near Sawgrass

2 min walk to pool, 4 seat cart, 5 min to Eastport

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

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Luxury home with a pool and 3 bedroom

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

The Villages Oasis w/ Golf Cart 2BR/2Bath
Condo rentals with a pool
Other vacation rentals with a pool

Beautifully Furnished 3/2 with In-ground Pool

StJohns is a great area for golf, hiking, Kayaking

Pool Home Great Location 3/2 & 2 Golf Carts

Spotless Villa Near Brownwood Sq- Lanai & King Ste

Perfect location Lake Sumpter Villa w/ Golf Cart

The Villages Spanish Springs Square

Welcome to the Villages

Slice of Paradise! Great location 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 |
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.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 7,790 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 110 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!
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