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.

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Top guest favorite
A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.
Home in The Villages
4.96 out of 5 average rating, 141 reviews

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

Top guest favorite
A private pool is enclosed within a screened lanai, surrounded by a spacious patio area. Comfortable seating is provided alongside the water, with views of the nearby lake and lush greenery under a partly cloudy sky. An inset image displays a red golf cart.
Home in The Villages
4.95 out of 5 average rating, 39 reviews

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.

Guest favorite
A golf cart is parked beside a modern villa, positioned on a pebbled driveway. A white picket fence outlines the property, and a garage door stands closed in the background. Clear blue skies provide a bright ambiance.
Home in The Villages
4.83 out of 5 average rating, 18 reviews

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.

Top guest favorite
Villa in The Villages
5 out of 5 average rating, 39 reviews

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

Top guest favorite
An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.
Home in The Villages
4.98 out of 5 average rating, 95 reviews

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.

Guest favorite
Home in The Villages
4.87 out of 5 average rating, 23 reviews

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.

Top guest favorite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages
5 out of 5 average rating, 112 reviews

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!

Top guest favorite
Home in Wildwood
5 out of 5 average rating, 19 reviews

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.

Guest favorite
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages
4.85 out of 5 average rating, 116 reviews

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.

Top guest favorite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 103 reviews

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.

Top guest favorite
An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.
Home in The Villages
4.96 out of 5 average rating, 143 reviews

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

Guest favorite
The open living area showcases a cozy red sofa facing a large TV mounted on the wall. A sleek kitchen bar with three red stools is situated nearby, and a chair with a patterned design complements the modern decor. Natural light is visible from an entrance.
Home in Lady Lake
4.89 out of 5 average rating, 64 reviews

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

When is the best time to visit The Villages?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ639ﺩ.ﺇ679ﺩ.ﺇ661ﺩ.ﺇ474ﺩ.ﺇ452ﺩ.ﺇ433ﺩ.ﺇ386ﺩ.ﺇ375ﺩ.ﺇ422ﺩ.ﺇ433ﺩ.ﺇ499ﺩ.ﺇ521
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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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