Vacation rentals with a pool in Lady Lake

4.96 out of 5 average rating, 134 reviews

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

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

5 out of 5 average rating, 22 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

Nestled amidst lush greenery and shrubs ,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. The flow between indoor and outdoor spaces offers an ideal retreat. Conveniently located, Vida Rosa is just a short golf cart ride away from the squares of Spanish Springs and Lake Sumter offering a variety of restaurants, shopping, and entertainment.

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, 46 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 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, 323 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, 407 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

4.99 out of 5 average rating, 146 reviews

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

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 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, 22 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 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, 49 reviews

Villages home with unique elevated front porch

A bright 2 bed, 2 bath home with new flooring throughout, includes golf cart. Located in historic Country Club Hills. Less than two miles from Spanish Springs Square with restaurants, shops & FREE nightly entertainment. Minutes away from pools, hot tubs, recreation centers, walking paths, & golf courses. Fully equipped kitchen with starter pack. Relax with a book & a drink on the breezy front porch with an overhead fan. Free Netflix, Peacock Premium & high speed internet. No checkout chores.

4.93 out of 5 average rating, 137 reviews

Home in The Villages

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 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, 90 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,

4.84 out of 5 average rating, 103 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.