House holiday rentals in Lady Lake

4.99 out of 5 average rating, 116 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

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, 330 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.

The exterior of a single-story villa is depicted, featuring a light-colored stucco facade and a two-car garage. Paved driveway curves towards the entrance, with decorative landscaping including a potted plant and stone accents. Windows are adorned with decorative arches, enhancing curb appeal.

4.95 out of 5 average rating, 158 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

A single-story home is showcased with a light exterior and an attached two-car garage. Neat landscaping featuring low-maintenance gravel and diverse shrubs surrounds the entrance. A clear blue sky and a few palm trees contribute to the inviting atmosphere of the property.

4.91 out of 5 average rating, 102 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

We love this home because the location is FANTASTIC! It's under a mile to Sumter Landing (walking distance for us :)). Also, new floors, paint, etc! The living room furniture is extremely comfortable! The kitchen has everything you need. The beds are comfortable and there is a tv in every room. (The second bedroom but needs your own Roku or Firestick!) There is a cart included which is the best way to see The Villages. We know you will love it here! Let us know if you have any questions.

A single-story home showcases a light-colored exterior and a welcoming front porch, bordered by a white picket fence. Neatly trimmed shrubs and grass surround the home, adding to the cheerful curb appeal. A paved driveway leads to a garage on the right.

4.95 out of 5 average rating, 175 reviews

Home away from home entire house

Located in an excellent area in the Chatham neighborhood, of the Bromley villas. This home offers easy access to restaurants, shopping and recreation. For nightly entertainment you're a short distance away from Lake Sumter land and Spanish Spring town Square where you will find many restaurants, grocery stores and free nightly live entertainment. This home is fully equipped with everything you need. Pets are allowed. Recreational guest passes included. Golf cart not included with reservation.

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!

4.97 out of 5 average rating, 180 reviews

A spacious wooden dock extends over the calm waters, surrounded by lush greenery. Several people are seated, enjoying a meal together. Lawn chairs are arranged comfortably, with trees reflecting off the clear surface of the water nearby, creating a serene atmosphere.

Home in Weirsdale

Beautiful House On the River, Kayaks, Large Dock!

Come relax by the river in this 3-bedroom, 2-bathroom vacation rental in Lady Lake, Florida. Recently built by our family in 2022, the home has a screened in back porch, a fire pit, WIFI, and is complete with a large private dock right on the Ocklawaha River. All that and it's located only 10 minutes from The Villages where you can shop and have fun. Centrally located 1-1/2 hours from Disney, Daytona beach, and Tampa. Lockbox key access is available for check-ins at any time of day.

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, 101 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.

4.99 out of 5 average rating, 158 reviews

Private, remodeled 3/2, Golf Cart - 4, Pizza Oven!

3-bedroom (sleeps 6), 2-bath home in The Villages with 2 golf carts! Screened & covered patio includes grill, pizza oven, fire table, outdoor seating, table and privacy - rare in The Villages! Access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

4.88 out of 5 average rating, 120 reviews

Home in Summerfield

Cozy 2 bedroom home near The Villages

This hidden treasure is conveniently located next to The Villages. Enjoy a well kept, updated single wide mobile home in a spacious lot. The fenced in yard is perfect for children and pets to run and play. Relax in the screened in porch and take in the peaceful neighborhood surroundings. Just a short jog from Lake Weir where you can enjoy fishing, boating and swimming. Take a day trip to Orlando and Tampa attractions, Daytona and Cocoa beaches.

5 out of 5 average rating, 10 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, 140 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 Lady Lake house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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

A single-story home with a light beige exterior is set against a clear blue sky. Lush palm trees and manicured landscaping surround the entrance, which features a paver driveway leading to a double-garage door. The overall setting reflects a serene neighborhood ambiance.

5 out of 5 average rating, 19 reviews

On The Links-4bd w/pool in Spanish Springs!

4.95 out of 5 average rating, 108 reviews

A charming single-story home is set on a lush green lawn, surrounded by trees and landscaping. A welcoming front porch features a swing and a bright blue door, adding a touch of color to the natural surroundings.

Home in Ocala

Ocala Oasis-3 Bedrooms and Heated Pool!

The living area features an open-plan design, showcasing a comfortable couch with accent pillows and a rustic coffee table. A modern dining table is positioned nearby, complemented by a well-equipped kitchen in the background. Large mirrors and soft lighting enhance the inviting space.

4.93 out of 5 average rating, 15 reviews

The Golfer's Escape

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

5 out of 5 average rating, 13 reviews

Heart of The Villages-guest pass for pool, golf

A welcoming facade of a single-story home is presented, featuring a combination of red brick and light-colored siding. An American flag is displayed at the entrance. Lush green grass surrounds the walkway, leading to a covered porch and large windows that allow natural light to brighten the interior.

4.95 out of 5 average rating, 21 reviews

Arcade Happy Place Near Spanish Springs Square

Weekly house rentals

A light blue home features a welcoming front porch with a screened entry, providing a view of the neatly manicured lawn. The driveway leads to a single-car garage, framed by flowering plants and greenery, with soft sunlight illuminating the exterior.

4.97 out of 5 average rating, 33 reviews

Relaxing home in The Villages

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 with a yellow exterior is set in a lush green yard. Sunlight brightens the front, showcasing a covered patio area with a striped awning. Low shrubbery lines the foundation, adding to the inviting outdoor space. A grill can be seen on the patio.

4.88 out of 5 average rating, 17 reviews

On the Golf Course near Country Club

The exterior of the house features a well-maintained facade with a covered porch and an American flag displayed. Neatly trimmed bushes border the pathway, leading to the entrance. A garage is visible to the right, along with a small decorative sign in the front garden.

4.96 out of 5 average rating, 24 reviews

Rare Find 3/2 in Orange Blossom

The home's exterior is framed by well-maintained landscaping, featuring palm trees and a manicured lawn. A flagpole displays the American flag, adding a patriotic touch. A spacious driveway leads to the entrance, while a glassed-in porch is visible on the front.

4.96 out of 5 average rating, 53 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

4.98 out of 5 average rating, 87 reviews

A charming cottage is nestled among lush greenery and palm trees. A concrete pathway leads to the entrance, flanked by vibrant plants in pots. Stairs ascend to the front door, inviting guests to explore the cozy interior.

Home in Leesburg

Waterfront cottage Haynes Creek

The exterior of a single-story villa features a light grey façade with a one-car garage and a well-maintained front yard. A white picket fence surrounds the property, complemented by tidy landscaping and a concrete driveway leading to the garage.

4.94 out of 5 average rating, 34 reviews

Delightful 2 bed/2 bath villa!

The exterior of the home is displayed, featuring a light-colored facade with a large garage door. A well-maintained driveway leads to the garage, accompanied by landscaped patches of shrubbery on either side. The sky is bright, with scattered clouds adding to the welcoming atmosphere.

5 out of 5 average rating, 43 reviews

Coastal 3/2 Home W/ Golf Cart in Cason Hammock

Private house rentals

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

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

5 out of 5 average rating, 27 reviews

The backyard features a well-maintained mini golf course alongside a wooden deck with seating. Lush green grass and decorative stones surround the area, with a playground structure visible in the background. Palm trees and natural foliage provide a serene atmosphere.

Home in Leesburg

Treasure Island Getaway Kayak and Mini Golf

4.96 out of 5 average rating, 81 reviews

A wooden deck surrounds the home, featuring seating areas with two vibrant chairs and a table centered around a fire pit. An umbrella provides shade for outdoor lounging. The exterior of the house displays a light beige siding with a door and window that allow natural light in.

Home in Weirsdale

Cheerful, two bedroom Animal loving home,

A single-story home with a warm yellow exterior features a brown tiled roof and a two-car garage. Lush green landscaping surrounds the entryway, with manicured bushes and a neatly trimmed lawn. Large windows allow natural light into the inviting living space.

4.97 out of 5 average rating, 30 reviews

Designer Home in the Villages

A charming home is set against a clear blue sky, featuring a brick-paved driveway leading to a two-car garage. Lush greenery surrounds the property, with neatly trimmed shrubs and trees framing the front entrance, offering welcoming curb appeal.

4.96 out of 5 average rating, 26 reviews

Lovely Largo Lantana

Superhost

5 out of 5 average rating, 3 reviews

Sunset Getaway - 3/2 dog friendly w/golf cart

A screened-in patio area showcases two hanging chairs with cozy cushioning, accompanied by a low coffee table. A lush green artificial lawn enhances the space, while a ceiling fan provides airflow. Beyond the screens, outdoor seating is visible under a shaded canopy.