Holiday rentals with a pool in The Villages

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.

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

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.

4.95 out of 5 average rating, 20 reviews

Charming Villages Retreat

Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

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.

4.98 out of 5 average rating, 157 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.

5 out of 5 average rating, 5 reviews

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.

A private screened patio features two reclining lounge chairs positioned beside a small table. The pool is visible nearby, while a lush green landscape with palm trees is observable through the screen, offering a serene outdoor space.

4.97 out of 5 average rating, 90 reviews

Private Pool with Sunset View in Monarch Grove

New home. In new village. Western sun exposure for your afternoons by the pool. Rest, relax, and enjoy your lifestyle in THE VILLAGES. Over 3000 clubs of activities, 30+ golf courses and country clubs 20+ public pools, plus your own private pool. 3 downtown squares of live entertainment 365 days a year. 40 minutes to DisneyWorld, Universal Studios, Orlando Florida. Everglades recreation center is 1 mile away and has 50 acres of outdoor activities. 21 miles of walking, biking trails.

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.

4.98 out of 5 average rating, 101 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.

Place to stay in The Villages

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.

5 out of 5 average rating, 117 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!

A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.

5 out of 5 average rating, 46 reviews

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!!

4.86 out of 5 average rating, 119 reviews

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

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.

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.

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.

4.86 out of 5 average rating, 263 reviews

An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.

Villa in The Villages

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!

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.

4.96 out of 5 average rating, 147 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.

5 out of 5 average rating, 19 reviews

Designer Home in The Villages, FL.

5 out of 5 average rating, 37 reviews

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

The exterior of a single-story home is shown, featuring a light-colored façade with multiple windows. A landscaped front yard includes a manicured lawn and decorative stones. A two-car garage with a driveway is visible on the right side. Palm trees are present in the surrounding area.

4.88 out of 5 average rating, 43 reviews

Beautiful Designer Home in The Villages Fl

A single-story home is depicted in a well-kept neighborhood, featuring a manicured lawn with palm trees and shrubs. Two vehicles, including a golf cart, are parked in the driveway, while a cloudy blue sky provides a serene backdrop.

4.95 out of 5 average rating, 104 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

4.92 out of 5 average rating, 12 reviews

Home with private pool, Tierra grande villas

4.9 out of 5 average rating, 93 reviews

A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.

Home in Wildwood

New, private pool getaway in The Villages, FL

A single-story home is presented with a light tan exterior and a double garage. Plants are arranged along the driveway, creating a welcoming approach. The clear blue sky features scattered clouds, adding to the peaceful setting. The well-maintained lawn provides a neat backdrop.

5 out of 5 average rating, 8 reviews

Serenity - In The Villages

A charming golf cart is parked on a concrete driveway, featuring a sleek design with a black canopy. The surrounding area is landscaped with greenery and flowers, complementing the residential home and two-car garage visible in the background.

5 out of 5 average rating, 12 reviews

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

Condo rentals with a pool

A comfortable living area features a spacious sofa adorned with colorful cushions and a glass coffee table. Natural light enters through large windows, illuminating the light wood floors. A ceiling fan and soft lighting create a relaxing ambiance, complemented by a nearby seating area.

Condo in Clermont

4.62 out of 5 average rating, 29 reviews

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

A large sign is displayed prominently, reading 'I Love Westgate' in bold letters. The sign is framed by lush palm trees and colorful landscaping, with a warm, inviting building visible in the background under a partly cloudy sky.

Condo in Kissimmee

1 Bedroom 5-Star Standard Resort Villa Near Disney

4.92 out of 5 average rating, 24 reviews

Condo in Inverness

Wafflemaker Waterfront condo 2BR full ensuite pool

The living area features two comfortable sofas adorned with decorative pillows, arranged around a patterned area rug. A dining set with wooden chairs is visible nearby, while a spiral staircase leads to the upper level. Ample natural light enters through multiple windows.

Condo in Inverness

4.81 out of 5 average rating, 67 reviews

Cypress Cove Waterfront Townhome

A large, colorful sign displaying 'I ♥ WESTGATE' is prominently placed in front of a multi-story building. Surrounding palm trees and landscaped greenery enhance the welcoming exterior of the Westgate Town Center. The backdrop features a clear blue sky with fluffy white clouds.

Condo in Kissimmee

Beautifal 2 Bedroom 5-Star Grand Villa

A large, colorful sign reading 'I Love Westgate' is prominently displayed in front of a multi-story building. The sign features a bold red heart, surrounded by lush palm trees and decorative landscaping that adds a tropical feel to the setting.

Condo in Kissimmee

1 Bedroom 5-star Grand Resort Villa Near Disney

Other holiday rentals with a pool

The living area features a light-colored sofa paired with two striped armchairs, arranged around a coffee table. Natural light streams in through vertical blinds, illuminating the space. A dining area with a chandelier and table for six is visible in the background.

5 out of 5 average rating, 18 reviews

Casa Bella: 3 Bedroom 2 Bath House Sleeps 6

The exterior of a single-story villa is highlighted, featuring a yellow facade with a two-car driveway and a well-maintained landscape. Lush green shrubs and palm trees are observed, alongside colorful planters that add vibrancy to the entrance.

4.93 out of 5 average rating, 92 reviews

Villa la Bella

A heated pool is featured with a smooth, curvaceous shape and clear water reflecting surrounding shadows. Access is provided by steps leading into the water. The pool area is enclosed by a screen, allowing views of the lush green yard and nearby homes.

5 out of 5 average rating, 47 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

4.89 out of 5 average rating, 45 reviews

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

An aerial view of the villa showcases its well-maintained exterior with a pitched roof and a combination of light yellow and gray hues. A screened lanai can be seen, along with a spacious outdoor patio area. Lush greenery and colorful flower beds enhance the welcoming curb appeal.

5 out of 5 average rating, 11 reviews

Slice of Paradise! Great location in The Villages!

Superhost

Home in Lady Lake

5 out of 5 average rating, 8 reviews

House on Golf Course, with Heated Pool & Golf Cart

4.88 out of 5 average rating, 8 reviews

The exterior of a modern single-story home is shown, featuring a light grey facade and a well-maintained front yard. A golf cart is parked in the driveway. A covered porch with seating is visible, complemented by two windows that bring natural light to the inviting entryway.

Home in Wildwood

Entire House in The Villages

The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.