Holiday rentals with a pool in Lady Lake

A bright yellow door features a decorative wreath made of colorful flip-flops and a large floral element. The door is framed by clear glass panels, with the words 'home sweet home' artfully displayed near the doorknob.

4.95 out of 5 average rating, 93 reviews

Magnolia Cottage under the Paradise sun.

Stay in my quiet neighborhood 1 hour/ 15 minutes from Disney. Enjoy the country club pools. Just five minutes away listen to free music every night at Spanish Spring Town Square. Restaurants & shopping are also minutes away. For your enjoyment there are recreation centers, golf courses & sports courts. Pickleball anyone! Roku TVs are located in the living room & bedroom. Log into your favorite apps. Take a bike ride on the bicycles. For your convenience there is a grill, laundry & free parking,

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, 137 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 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, 331 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.

4.98 out of 5 average rating, 418 reviews

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guesthouse in Leesburg

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

4.93 out of 5 average rating, 138 reviews

Pool, golf cart, private backyard. Paradise!

Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

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, 105 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, 113 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, 102 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.

4.91 out of 5 average rating, 11 reviews

The Villages Oasis

Welcome to The Villages Oasis! This charming villa offers a relaxing getaway with its private pool and hot tub. Enjoy comfortable accommodations with two bedrooms, a fully equipped kitchen, and convenient amenities like air conditioning and Wi-Fi. Located on Morse Road just a 5 minute drive from Spanish Springs, you'll have easy access, shopping, and more. Enjoy the perfect blend of relaxation and recreation in this beautiful Florida retreat.

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, 141 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

A single-family home is depicted with a large driveway leading to a two-car garage. A covered front porch with white railings is visible, framed by neatly trimmed shrubs. The exterior features light-colored siding and blue window shutters, set against a backdrop of a well-maintained lawn.

4.95 out of 5 average rating, 19 reviews

Welcome to the Villages

Beautiful Single family home perfectly located within a mile and a half from Lake Sumter Landing and Spanish Springs. Pool and recreation center is within walking distance. The Villages is a gated community with numerous amenities, Golf carts available for a small fee. There are numerous activities for everybody here in The Villages, your home away from home .

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, 103 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

Nestled in Winifred Village, this beautifully adorned home is a gem in The Villages. A quick golf cart ride to Lake Sumter Landing and the Polo Field, and backing onto the Arnold Palmer Golf and Country Club, it's a golfer's paradise. Plus, a pool is just a short walk or a minute's cart ride away!

Popular amenities for Lady Lake rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A cozy living area features two gray sofas adorned with decorative blue and white throw pillows. A wooden coffee table with a colorful centerpiece sits atop a patterned rug. Natural light enters through sliding glass doors, enhancing the inviting ambiance.

4.97 out of 5 average rating, 39 reviews

Oasis in Heart of The Villages

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, 152 reviews

Whole House-sleeps 10 The Villages Spanish Springs

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

The exterior of a single-story home is framed by three tall palm trees, set against a clear blue sky. A well-maintained lawn surrounds the entrance, which is highlighted by a neatly paved driveway and a two-car garage. The inviting front door features a large window.

5 out of 5 average rating, 25 reviews

The Mulligan House-The Villages

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

A one-story home with a light pink exterior is depicted, featuring a spacious driveway and a well-maintained lawn with green grass. Two garage doors are visible, along with several windows that enhance natural light. Tall palm trees are present in the background.

5 out of 5 average rating, 21 reviews

The Villages Spanish Springs Square

4.96 out of 5 average rating, 82 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.

4.97 out of 5 average rating, 31 reviews

A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.

Home in Wildwood

Brownwood Square - Villages Home

Condo rentals with a pool

A cozy living area is presented with a sectional sofa in a rich blue fabric, accented by decorative pillows. A low coffee table holds a decorative tray with candles and flowers. A small pink chair adds a playful touch. Natural light filters through sheer curtains.

Condo in Altamonte Springs

5 out of 5 average rating, 5 reviews

Modern & Quiet High-rise

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

A comfortable living area features a dark sofa adorned with colorful throw pillows. Natural light enters through two windows with wooden blinds. A small coffee table and a soft ottoman complement the cozy atmosphere. Indoor plants add a touch of greenery to the space.

Condo in Dunnellon

EarlyTimes on the Withlacoochee!

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

An open living and dining area features a modern glass dining table surrounded by four chairs. A comfortable seating arrangement is situated nearby, illuminated by natural light from sliding glass doors that lead to an outdoor space. Soft décor elements create a welcoming environment.

Condo in Hernando

Walk to Citrus Hills Golf Club: Condo w/ 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!

4.82 out of 5 average rating, 17 reviews

A serene swimming pool area is framed by lush greenery and overlooks a calm body of water. Comfortable blue lounge chairs are arranged around the pool, complemented by potted plants. The clear sky and surrounding nature create a peaceful outdoor setting.

Condo in Dunnellon

River Retreat

Other holiday rentals with a pool

A private in-ground pool is enclosed by a screen patio, featuring a textured stone deck. Comfortable lounge chairs line the poolside, with a railing leading into the water. Lush greenery surrounds the area, offering a sense of tranquility and seclusion.

4.94 out of 5 average rating, 48 reviews

Beautifully Furnished 3/2 with In-ground Pool

4.91 out of 5 average rating, 87 reviews

An enclosed pool area features a large, well-lit swimming pool with turquoise water. A water slide is positioned on one side, while the background showcases lounge seating and a bar area illuminated in soft blue light.

Guest suite in Leesburg

Smoke free Allergen Free unit. Animals Not Allowed

A green golf cart is parked on a stone driveway in front of a light-colored house. The cart features a canopy and seating for four, with two spacious seats in the front. The garage door is seen in the background, providing additional context of the home.

4.91 out of 5 average rating, 69 reviews

KingBed w/Cart

Superhost

5 out of 5 average rating, 3 reviews

Sunset Getaway Eastport dog friendly w/golf cart

An open-plan living area features a comfortable light-colored sofa situated near a wooden coffee table on a patterned rug. A large smart TV is mounted on the wall across from the seating. Natural light enters through sizeable windows, creating a bright and airy space.

4.93 out of 5 average rating, 15 reviews

The Golfer's Escape

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

4.97 out of 5 average rating, 69 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