Vacation 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, 138 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.

4.94 out of 5 average rating, 18 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.

The exterior of a spacious single-story house is visible, featuring a light-colored facade and a greenery-laden yard. A palm tree is seen in the foreground, while the driveway leads towards a garage on the right side.

4.92 out of 5 average rating, 144 reviews

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

Live Music on the Square. Golf , Pools, tennis, etc Spacious 3 bedroom house in The Villages. The house has a hot tub on the back lanai. The house is newly renovated and features both a new 70 inch Samsung TV in the living room and a new 50 inch Samsung TV in the master bedroom with Hulu Live and Comcast Business high speed internet. The house is located near the Spanish Springs Town Center and Glenview Country Clubs. The home sleeps 8 with privacy using a sofa bed located in the rec room.

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

4.96 out of 5 average rating, 335 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

4.97 out of 5 average rating, 73 reviews

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

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.

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, 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!

4.85 out of 5 average rating, 114 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.

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

Welcome to your dream retreat! This stunning Moonstone Home blends comfort, luxury, and convenience. Minutes from Eastport Square, Publix, and Fenney Rec Center, enjoy nature trails, pools, Fenney Grill, and executive golf—all accessible by golf car. Relax in the private lanai, cook in the chef’s kitchen, or watch SpaceX launches from your patio. With mossy oaks, stylish design, and top amenities, your perfect Villages getaway awaits. Book now and experience the magic!

4.97 out of 5 average rating, 88 reviews

A single-story house features a white exterior with a gabled roof and a two-car garage. A white picket fence and manicured shrubs border the front yard, while a concrete driveway provides ample parking space. Clear blue skies are visible in the background.

Home in Wildwood

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

A well-maintained exterior features a single-story villa with light grey siding and a simple gable roof. A gas cart is parked on the driveway, surrounded by neatly trimmed shrubs and gravel landscaping, adding to the property’s welcoming ambiance.

4.96 out of 5 average rating, 139 reviews

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly

Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.

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, 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 18 reviews

A wooden boardwalk winds gracefully along the edge of a tranquil waterway, surrounded by lush greenery and mature trees. Nearby, a pavilion stands, offering shaded views of the serene landscape, enhancing the outdoor experience.

Home in Wildwood

StJohns is a great area for golf, hiking, Kayaking

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

5 out of 5 average rating, 55 reviews

Villages home with unique elevated front porch

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.

4.89 out of 5 average rating, 64 reviews

The Villages, De La Vista West 1762

4.97 out of 5 average rating, 30 reviews

Spotless Villa Near Brownwood Sq- Lanai & King Ste

The image showcases a sparkling blue pool surrounded by a spacious screened enclosure. A jacuzzi is integrated at one end, and golf course views are visible through the greenery. Lounge chairs are positioned around the pool area, providing a relaxing outdoor space.

4.85 out of 5 average rating, 48 reviews

Get it all - Pool, Jacuzzi, Golf View, & Golf Cart

An aerial view showcases a charming villa with a well-manicured lawn. The property features a spacious driveway, a screened lanai, and tasteful landscaping, including shrubs and palm trees. Nearby homes can be seen, contributing to a cohesive community layout under clear skies.

5 out of 5 average rating, 13 reviews

Patio Villa - Pet Friendly 2/2 Home (South of 44)

4.9 out of 5 average rating, 50 reviews

Gem in the Villages! Free golf cart with waiver

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.

4.83 out of 5 average rating, 18 reviews

2/2 Villa 5 min from Lake Sumter Landing-pets

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

4.59 out of 5 average rating, 27 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

4.89 out of 5 average rating, 19 reviews

Condo in Inverness

Wafflemaker Waterfront condo 2BR full ensuite pool

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 vacation rentals with a pool

Superhost

A inviting living room features a comfortable seating arrangement with a green armchair and a blue accent chair. A colorful area rug lies on the hardwood floor, while natural light enters through large windows. A TV is positioned on a low wooden unit, with a decorative table beside it.

4.89 out of 5 average rating, 38 reviews

The Villages 4 Golf, PickleBall & a whole lot more

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, 46 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

5 out of 5 average rating, 24 reviews

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

Heated Pool Golf Cart Dog Friendly in The Villages

5 out of 5 average rating, 14 reviews

Heart of The Villages-guest pass for pool, golf

5 out of 5 average rating, 11 reviews

Lazy Day Getaway*New Const*2bd/2ba*Pet Friendly

A heated pool is enclosed within a screened patio, featuring gentle water features and surrounded by lush greenery. Two wooden adirondack chairs and a small side table are positioned nearby, inviting relaxation in this outdoor space.

5 out of 5 average rating, 16 reviews

The Villages, Heated Pool Walk to Sawgrass

4.86 out of 5 average rating, 74 reviews

Aerial view of the villa displays a well-maintained exterior with palm trees and landscaped shrubs. The driveway leads to a garage, and a circular pathway connects to a fenced yard, enhancing the tranquil outdoor space.

Villa in The Villages

AMAZING Location! Villa Near Lake Sumter Landing

A single-story home is showcased with a well-maintained front yard, featuring manicured grass and small landscaping elements. The exterior is designed with a light-colored facade, and large windows reflect the evening sky's hues. A two-car garage is included, along with a spacious driveway.