Vacation rentals with a pool in Lady Lake

A heated pool is enclosed in a screened lanai, featuring a modern design with clear water reflecting evening lights. Surrounding areas are adorned with soft lighting, enhancing the relaxing ambiance. The pool deck is finished in smooth tiles, providing ample space for lounging.

4.95 out of 5 average rating, 126 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 spacious ranch-style home is set within a large green lawn, featuring light-colored exterior walls and a brown roof. The front porch is accessible from the centrally located entrance, surrounded by a wooden fence and lush trees that provide a sense of seclusion.

5 out of 5 average rating, 30 reviews

Ranch Retreat~10 beds~New

This ranch retreat home is perfect for large groups with plenty of parking. Perfect for celebrations, family gatherings, and even corporate or church events. Located on a large parcel of land in Lady Lake, FL, this home offers a quiet and secluded location that is centrally situated near the Villages and Chain of Lakes. We are 5 minutes away from Lake Griffin boat ramp, minutes away from Lake Griffin State Park, within 15 minutes of Venetian Gardens/Ski Beach and Lake Harris, and Eatons Beach.

A sparkling blue pool is centered in a landscaped area, bordered by a smooth concrete deck. Lush greenery and colorful flowers create a serene atmosphere. A shaded seating area is visible in the background, enhancing the inviting outdoor space.

4.96 out of 5 average rating, 313 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, 389 reviews

The pool area features a large saltwater pool with a paved deck. Several white lounge chairs are arranged near the water, and the back of the property is adorned with windows that provide natural light. Lush greenery surrounds the area, enhancing the tranquil setting.

Guesthouse in Leesburg

Silver Lake Guest Pool House

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

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.

4.99 out of 5 average rating, 141 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.

The exterior of a newly constructed home is highlighted by three tall palm trees, flanking a neatly landscaped area with colorful flowers. A driveway leads to a garage, while a smooth concrete pathway provides access to the front entrance under a partly cloudy sky.

5 out of 5 average rating, 16 reviews

The Mulligan House-The Villages

BRAND NEW Golf-Front Furnished Home for rent- "Million Dollar View" This 3 bedroom 2 bathroom home sits on the 18th fairway of Orange Blossom Hills Championship Golf Course!! Enjoy panoramic GOLF COURSE VIEWS from the Great Room. Kitchen, Screened Lanai and from your Master Suite. Located within WALKING DISTANCE from the Orange Blossom Hills Country Club with its RESORT STYLE POOL. A short golf cart ride over the bridge brings you into Spanish Springs with Shopping, Dining and entertainment.

The screened outdoor area features a small plunge pool surrounded by a spacious patio. Bright blue chairs are positioned nearby, creating a relaxing space. A table with two glasses rests between two woven chairs, complemented by a cozy seating arrangement, all set against a backdrop of lush greenery.

4.93 out of 5 average rating, 134 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!

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.

4.91 out of 5 average rating, 34 reviews

The Villages 4 Golf, PickleBall & a whole lot more

Our home has everything you need for comfort & ease when you are not out enjoying "The Villages Lifestyle". It is on the "Historic Side". Walk to Spanish Springs Town Square, Publix, restaurants & shopping. Paradise Park is a short walk away where you can enjoy the shaded pathways. Hang out at the archery field or take in some self guided exercise with outdoor equipment. So much to enjoy so little time to take it all in! Note: The Villages is an active adult community. No work crews.

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.

4.94 out of 5 average rating, 85 reviews

Magnolia Cottage under the Paradise sun.

Stay in my quiet neighborhood 1 hour and 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! New Roku TVs are located in the living room & bedroom. Take a bike ride on the bicycles. For your convenience there is a new grill, laundry & covered free parking,

A serene patio area features a heated saltwater pool enclosed within a birdcage screen, offering privacy. Comfortable seating is provided nearby, along with a small table. Lush greenery surrounds the pool area, enhancing the tranquil setting.

4.95 out of 5 average rating, 126 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

4.96 out of 5 average rating, 68 reviews

A refreshing swimming pool features vibrant blue water, with a yellow inflatable float resting on the surface. A set of white pool steps is visible at the edge, leading to the inviting water. Lush greenery frames the pool area, adding a tranquil touch.

Tiny home in Lady Lake

Hummingbird Cottage Pool/Hot tub

This unique place has a style all its own. Cottage is thoughtfully decorated to match the backyard tropical paradise. On-site 20 x 20 Tiki hut and Pool Cabana with Jamaican chef to make your meals (surcharge). Registered guests can relax in the private hot tub, and pool. Property is completely private with flower gardens and water fountains for bird watching. There are many shaded sitting areas for reading and relaxing.

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.