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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Guest favorite
Home in The Villages
5 out of 5 average rating, 8 reviews

5-Star Luxury | Prime Location & Top Amenities

WITH GOLF CART IN THE VILLAGES TOTALLY REMODELED NO PETS in the heart of The Villages 2 bedrooms ,2-baths 2, TVS Every inch of this home has been updated with luxury vinyl plank flooring, and a fully equipped high-end kitchen with quartz countertops new cabinets, new stainless NEW steel appliances bedrooms newly renovated a king-size bed second bedroom a queen-size bed. 2 bathrooms completely renovated just minutes from Lake Sumter Landing and Spanish Springs Town Square ,entertainment,

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 single-story home is situated on a corner lot, surrounded by well-maintained lawns and landscaping. Large trees provide shade, while the blue sky creates a bright backdrop. A screened-in porch and patio area are visible on the side of the house.
Home in The Villages
4.98 out of 5 average rating, 155 reviews

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Top guest favorite
An expansive pool area features a sparkling blue pool and a relaxing spa surrounded by a screened enclosure. Lush green trees reflect in the tranquil pond visible beyond the outdoor space, creating a serene backdrop. Two comfortable lounge chairs sit nearby under a shaded awning.
Home in Wildwood
5 out of 5 average rating, 15 reviews

Poolside Paradise-w/ Pool & Golf Cart The Villages

Welcome to Poolside Paradise! Your dream getaway in a fantastic location within The Villages, FL. Nestled in The Village of Chitty Chatty, this stunning 4-bed, 3-bath retreat is your ticket to ultimate relaxation and fun. Explore the vibrant surroundings with ease, thanks to the complimentary 4-seater golf cart provided for your convenience. There are four (4) bikes available for guest use as well. You will have easy access to multiple recreation centers, town squares, & entertainment venues.

Guest favorite
The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.
Villa in Lady Lake
5 out of 5 average rating, 24 reviews

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 .

Guest favorite
A serene outdoor space is presented, featuring comfortable lounge chairs with turquoise cushions and a cozy seating area adorned with patterned pillows. A low table holds potted flowers, and soft lighting drapes overhead, enhancing the ambiance of the screened space.
Home in The Villages
4.96 out of 5 average rating, 45 reviews

Sea Horse House

Relax in the screened, PRIVATE, heated saltwater lap pool. Pool towels included, or Pay a one time fee of $50. to transfer membership and use all the Villages amenities for 89 community pools and rec centers. golf on 55 courses, 2 Country Clubs for Tennis, Pickle Ball, join a club, play cards. Brand New King Beds with 100% organic cotton sheets, Brand New Samsung Flat Screen TVs in every room, X-finity Wi-Fi incld. All new appliances, Wine & Juice bar adjacent to the coffee bar, W/D

Top guest favorite
A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.
Home in Wildwood
4.97 out of 5 average rating, 74 reviews

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.

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, 113 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!

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, 117 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

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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