Family-friendly vacation rentals in Lady Lake

4.99 out of 5 average rating, 108 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!

5 out of 5 average rating, 19 reviews

An open living space features a cozy sleeping area and a small dining arrangement. Wooden beams highlight the ceiling above. Natural light enters through the door and windows, while a television and kitchenette with appliances are visible against the walls.

Apartment in Lady Lake

Desperado 2 - Cozy Peaceful Apt. Lady Lake FL.

Escape to your unique and private 2nd story apartment nestled on 2 acres of serene land and just a short 7-minute drive to The Villages. Enjoy the tranquility of nature while still being close to vibrant entertainment, shopping and dining options. Your cozy and well appointed space offers the perfect blend of seclusion and convenience making it an ideal getaway for relaxation and rejuvenation. *perfect for vacation *perfect for traveling workers *perfect for visiting family in the The Villages

4.96 out of 5 average rating, 325 reviews

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.

Home in Lady Lake

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, 151 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

4.98 out of 5 average rating, 410 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

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, 150 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.

4.92 out of 5 average rating, 150 reviews

A well-lit bedroom features a spacious bed made with white linens, complemented by bedside tables and lamps. Two chairs are positioned alongside the bed. Art depicting landscapes hangs above the bed, while light filters through a window adorned with white blinds and red curtains.

Apartment in Belleview

Solomon's porch entire apartment

Solomon's porch apartment is entire private 350 st ft apartment with bedroom, kitchenette, your own hallway and private bathroom. Solomon's porch apartment attached to main house.We are small Christian family that loves bible proverbs and named Airbnb after Solomon's wisdom. We have other listing that we are hosting since 2022. Our brand new house located between Ocala and The Villages. We are only few minutes from Santos mountain bike trails, horse park, National Forest and Silver Springs.

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, 171 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.

A well-maintained home is visible, with a neatly landscaped driveway leading to a garage. An orange golf cart is parked prominently in front, surrounded by lush green grass and a manicured shrub nearby. A white picket fence adds charm to the yard.

4.98 out of 5 average rating, 120 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

4.93 out of 5 average rating, 137 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!

4.96 out of 5 average rating, 167 reviews

Cottage in Coleman

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

4.88 out of 5 average rating, 112 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.

Popular amenities for Lady Lake family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 107 reviews

The interior of the tiny house features a modern kitchen equipped with stainless steel appliances and a compact dining area with stools. A cozy sleeping loft with twin beds is visible, while light filters through the windows, creating a bright and airy atmosphere.

Tiny home in Clermont

Pet Friendly, Modern Tiny Home in Clermont!

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, 17 reviews

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

4.88 out of 5 average rating, 80 reviews

A custom home is framed by lush greenery and mature trees. The landscaped yard features a manicured lawn, and the house showcases a welcoming façade with multiple windows, allowing natural light to enhance its inviting presence.

Home in Summerfield

A+ Privacy | Hot Tub | BBQ + Dining | Family +Pets

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.

4.94 out of 5 average rating, 17 reviews

Welcome to the Villages

Superhost

The exterior of the house features a charming white facade with black window frames. A welcoming entrance is highlighted by a central archway and a stylish light fixture. A spacious driveway leads to the entrance, flanked by neat landscaping and a covered parking area.

Home in Ocala

4.89 out of 5 average rating, 149 reviews

Modern Colonial+3 baths and Hot tub+ Pet Friendly

4.85 out of 5 average rating, 172 reviews

A tranquil log cabin is nestled among lush greenery, with a wooden deck extending over calm waters. The surrounding trees provide shade, while the cabin's rustic exterior blends harmoniously with the natural environment, creating a serene retreat.

Cabin in Brooksville

Log cabin on the river

4.99 out of 5 average rating, 151 reviews

A zebra is seen standing in a lush green pasture surrounded by trees. The animal's distinctive black and white stripes contrast with the vibrant grass. Fencing is visible in the background, providing an enclosure for the pasture.

Farm stay in Pierson

Ruby Oaks Farm w/ Beach Near St. JohnsRiver

A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.

5 out of 5 average rating, 36 reviews

Pirates & Parrots - The Villages - w/Golf Car !

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 125 reviews

A set of wooden steps leads up to a charming cottage nestled among trees. The entrance features large glass doors, inviting natural light into the space. The surrounding area is landscaped, enhancing the tranquil ambiance of the private property.

Cottage in Eustis

Redbird cottage and farm. Equestrian lake cottage

4.98 out of 5 average rating, 83 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

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, 136 reviews

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

4.97 out of 5 average rating, 175 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!

5 out of 5 average rating, 23 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

4.95 out of 5 average rating, 287 reviews

The exterior of the house is presented at dusk, showcasing well-manicured grass and landscaping. Soft lighting highlights the entrance and garage. A welcoming front porch is visible, framed by trees in the background, creating a serene environment.

Home in Leesburg

Peace and Quiet

A single-story home features a simple façade with a covered entryway and a spacious driveway. Lush green grass borders the driveway, complemented by small landscaping elements. The neighborhood displays well-maintained properties on either side, under a clear blue sky.

4.97 out of 5 average rating, 59 reviews

The Sunshine Retreat with Golf Car

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

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 37 reviews

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.

Home in Lady Lake

The Villages 4 Golf, PickleBall & a whole lot more

4.9 out of 5 average rating, 83 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

Mid Century Living on Lake Eustis. Dock available.

Guesthouse in Deer Island

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

4.95 out of 5 average rating, 127 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

4.95 out of 5 average rating, 103 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!

4.84 out of 5 average rating, 105 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!

The exterior of the home displays a well-manicured front yard with decorative plants and a white picket fence. A paved driveway leads to a two-car garage featuring a symmetrical design, accompanied by a clear blue sky above.

4.96 out of 5 average rating, 89 reviews

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

4.98 out of 5 average rating, 40 reviews

A gray pickup truck is parked along a paved driveway in front of two nearby houses. Lush greenery surrounds the area, contributing to a spacious neighborhood vibe. Clear skies provide ample natural light, enhancing the scene of this welcoming residential setting.

Home in Leesburg

Luxury home with a pool and 3 bedroom

A single-story home is set against a bright sky with sun rays radiating. The front yard includes a white picket fence and a tropical palm, with gravel landscaping contrasting against the lush green lawn.