Family-friendly holiday rentals in Lady Lake

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.

4.95 out of 5 average rating, 147 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, 346 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.

4.99 out of 5 average rating, 103 reviews

Virginia Trace | 1 mile to square, walk to pool

1 mile from Lake Sumter Town Square Virginia Trace Villa has everything you need in this updated 3 BR, 2 bath 1740 sq ft villa. A perfect space centrally located to explore The Villages. The villa features a spacious LR area w/ a 65" smart TV, fully stocked kitchen, 2 dining areas, & screened in patio where guests can relax & enjoy the sitting area. In unit washer & dryer. Wifi & parking included. Golf cart accessible. Guest passes available upon request (provide info 3 days prior to check-in).

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, 159 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.

4.85 out of 5 average rating, 127 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, 103 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.

A comfortable living area features a light-colored sectional sofa and a textured rug. A wall-mounted television is positioned above an elegant gray console table adorned with small potted plants. Soft lighting is provided by pendant lamps, complemented by natural light from a nearby window.

4.95 out of 5 average rating, 88 reviews

Villages, FL. Designer Home 2 blocks from town SQ!

Location!Location! Location! Designer home with access to close shopping,pools, tennis, golf, pickle ball, live bands every night, and it’s all within 5 minutes on golf cart! High speed Wifi. Grocery stores are 2 blocks from house! Golf cart is included with house. The house is located one hour north of Orlando, and 1 hour and 9 minutes away from Disney World! There is so much to do here in The Villages you can find something of interest for everyone in the family! Enjoy!

4.99 out of 5 average rating, 170 reviews

Private 3/2, 2 Golf Carts, Pizza Oven, Game Table!

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.

5 out of 5 average rating, 246 reviews

Guesthouse in Lady Lake

Cute & Cozy Tiny Guesthouse

Take it easy at this cozy and peaceful getaway located in a safe and quiet neighborhood near The Villages. It's conveniently located all within 1.5 miles to Walmart, Aldi, Waffle House, McDonald's, Pizza Hut, Cracker Barrel, BJ's Wholesale and many other shops and restaurants. Plus, The Villages Hospital. We are also located two miles from The Villages Spanish Springs town square which has free entertainment from 5pm to 9pm every night of the week.

4.97 out of 5 average rating, 71 reviews

The Promise Land~10 beds~New

Set on 158 breathtaking acres in Lady Lake, FL, our scenic home features rolling green pastures, majestic oak trees, and stunning sunsets that create the perfect backdrop for unforgettable weddings, elopements, and special events. With wide-open natural landscapes, abundant wildlife, and peaceful surroundings, it’s an ideal setting for ceremonies, receptions, retreats, and celebrations just minutes from The Villages and about an hour from Orlando.

4.92 out of 5 average rating, 26 reviews

Private Pool and Hot Tub in The Villages

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, 152 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 family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 61 reviews

Villages home with unique elevated front porch

4.95 out of 5 average rating, 115 reviews

Apartment in Ocala

Cute cottage-historic district-hot tub

4.98 out of 5 average rating, 171 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

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, 127 reviews

Safari themed private addition with pool/hot tub.

A single-story villa is displayed with a light beige exterior and a neatly paved driveway. The two-car garage is situated on the left side, while manicured hedges and green grass create an inviting approach to the front entrance.

4.74 out of 5 average rating, 152 reviews

3 bdrm 2 ba fully furnished!

Campervan/RV in Fort McCoy

A clear, tranquil spring with vibrant green waters is surrounded by lush greenery. Several people are enjoying the water, while a couple of individuals sit on a concrete edge, facing the spring. Scenic viewing areas are visible along the water's edge.

4.88 out of 5 average rating, 354 reviews

5 local springs, Gated Resort in Ocala Forest

4.83 out of 5 average rating, 103 reviews

The exterior of the home features elegant curved architecture, complemented by a vibrant red front door. Large arched windows allow natural light to fill the interior, while the well-manicured lawn and landscaping enhance the welcoming feel of the property.

Home in Ocala

Elegant Ocala Oasis w/Pool: Unwind in Luxury

4.85 out of 5 average rating, 191 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

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 147 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

4.97 out of 5 average rating, 214 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!

4.95 out of 5 average rating, 170 reviews

A spacious living area is equipped with two reclining armchairs and a comfortable sofa, arranged around a glass coffee table. A flat-screen television is positioned on a white media console. Natural light filters in through large windows, enhancing the welcoming environment.

Home in Inverness

Inverness 2/2 Fenced Yard w/Hot Tub Availability

A screened lanai features comfortable seating and is positioned adjacent to a well-maintained backyard. A tree is situated in the grassy area, providing shade, while a concrete pathway leads to the entrance. A white fence encloses the yard, enhancing privacy.

4.92 out of 5 average rating, 154 reviews

Briar Meadow Villa - Dogs are welcome!

The exterior of the home features a well-maintained front yard with manicured shrubs and palm trees. A golf cart and bicycle are parked on the driveway, with a two-car garage visible. The atmosphere is bright under a partly cloudy sky.

5 out of 5 average rating, 27 reviews

Walking distance to Lake Sumter Landing!- Magnolia

4.95 out of 5 average rating, 127 reviews

A rustic bedroom features a uniquely designed wooden bed with natural log accents and decorative pillows. Complementary wall art and hanging plants create a cozy atmosphere. Light streams in through horizontal blinds, adding warmth to the natural wood and brick elements of the room.

Cabin in Ocklawaha

Countryside Loft at Coco Ranch

4.95 out of 5 average rating, 308 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 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.

4.96 out of 5 average rating, 188 reviews

Home away from home entire house

Family-friendly home rentals with a pool

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.

4.9 out of 5 average rating, 68 reviews

The Villages, De La Vista West 1762

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, 55 reviews

Get it all - Pool, Jacuzzi, Golf View, & Golf Cart

5 out of 5 average rating, 26 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

5 out of 5 average rating, 13 reviews

Pool House Near Eastport and Middleton

5 out of 5 average rating, 16 reviews

A single-story villa is set against a backdrop of dramatic dark clouds. The light-colored exterior is complemented by a well-maintained green lawn. A white picket fence surrounds the property, with a gravel pathway leading to the entrance and a screen porch visible in the foreground.

Villa in Lady Lake

Heart of The Villages

4.92 out of 5 average rating, 49 reviews

Home in Fruitland Park

Luxury home with a pool and 3 bedroom

4.94 out of 5 average rating, 17 reviews

Home with private pool, Tierra grande villas