Family-friendly holiday rentals in The Villages

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, 327 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, 154 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 residence is depicted with a light-colored facade and a covered front porch. A golf cart is parked in the driveway, highlighting the golf cart-friendly community. Lush green grass surrounds the home, offering a well-maintained exterior in a tranquil neighborhood.

4.99 out of 5 average rating, 156 reviews

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

3-bedroom (sleeps 6), 2-bath home in The Villages! 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. Use 2023 4-seat gas golf cart or 3 bikes to get to it all! Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

Serviced apartment in Belleview

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.

4.92 out of 5 average rating, 153 reviews

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 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, 60 reviews

The Sunshine Retreat with Golf Car

Come and enjoy this beautiful 2 Bed/2 Bath Patio Villa Home. We have made it very relaxing and welcoming for your stay. You will enjoy just a 3 minute golf car ride to Sawgrass, 15 minute golf car ride to new Eastport and a 20 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about a 5 minute golf car ride away. Golf Car included with home. Renter assumes all liability and will be responsible for any damage or injury caused by the use of the golf car.

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, 98 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

4.84 out of 5 average rating, 107 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, 99 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.

The exterior of a single-story home is showcased, featuring a well-maintained lawn and a gravel pathway. A seating area with chairs is positioned on the front porch. The garage is visible on the right, and colorful clouds are present in the evening sky.

5 out of 5 average rating, 12 reviews

Incredi-Bill Jo's

Get ready for an incredible stay at our Incredi-Bill Jo's stylish and cozy pool home. You'll be steps away from world class shopping, dining, entertainment, sports, recreation and GOLF. This three bedroom home is close to all of the amenities that make The Villages the number one destination for active adults year after year. And to make your stay even more incredible, you'll have the convenience and use of a beautiful golf cart! Come and see what all the fuss is about!

4.96 out of 5 average rating, 170 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.

5 out of 5 average rating, 5 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.

Popular amenities for The Villages 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!

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, 52 reviews

Villages home with unique elevated front porch

4.93 out of 5 average rating, 129 reviews

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

Spacious Bungalow with Private Pool and Courtyard

4.98 out of 5 average rating, 146 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

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

4.89 out of 5 average rating, 151 reviews

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

Modern Colonial+3 baths and Hot tub+ Pet Friendly

4.98 out of 5 average rating, 50 reviews

The home's exterior features a vibrant orange facade with a neatly manicured yard and landscaping of tropical plants and colorful stones. A golf cart is parked in the driveway, providing convenient access to nearby amenities.

Villa in The Villages

Courtyard Villa On Golf Course w/Cart & Hot Tub

4.85 out of 5 average rating, 174 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

4.95 out of 5 average rating, 43 reviews

The exterior of a charming cottage is highlighted, featuring a welcoming front porch with a single chair. Light-colored siding contrasts with dark shutters, and a decorative wreath adorns the door. Surrounding open fields and a fenced yard enhance the rural setting.

Farm stay in Belleview

Farm Stay at The Cottage

A modern single-story house is presented with a spacious driveway, flanked by lush green grass. A palm tree adds tropical appeal to the front yard, while a golf cart is parked to the left, contributing to the home's functional charm.

4.98 out of 5 average rating, 54 reviews

Villages-Waterfrnt, 3 king bds/2.5Ba+golf crt

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, 137 reviews

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

4.99 out of 5 average rating, 110 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!

5 out of 5 average rating, 17 reviews

A two-story home features a light blue exterior with a white garage door. A staircase leads to a front balcony above, while the driveway is lined with greenery and decorative stones. Surrounding trees provide a natural backdrop, enhancing the home's outdoor appeal.

Flat in Wildwood

Balcony Oasis Home

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.

4.97 out of 5 average rating, 32 reviews

Pet Friendly in the Villages!

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

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.

4.93 out of 5 average rating, 14 reviews

Charming Villages Retreat

Family-friendly home rentals with a pool

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, 24 reviews

The Mulligan House-The Villages

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.

4.95 out of 5 average rating, 22 reviews

Spotless Villa Near Brownwood Sq- Lanai & King Ste

5 out of 5 average rating, 16 reviews

A screened-in lanai features a heated pool with clear blue water, surrounded by a comfortable outdoor seating area. Two loungers and a table with chairs are visible, along with potted greenery enhancing the space. A view of the fenced yard and neighboring homes can be seen.

Home in Wildwood

Family Tides 3 Richmond

The front of a single-story home is presented, featuring a covered porch with two colorful chairs. A decorative mailbox is visible, and a blue truck is parked in the driveway. The lawn is neatly maintained, with shrubs lining the walkway.

4.98 out of 5 average rating, 49 reviews

Relaxing House in The Villages

4.97 out of 5 average rating, 64 reviews

A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.

Home in Wildwood

Newer Villa in The Villages near Brownwood

4.98 out of 5 average rating, 413 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.

Guest house in Leesburg

Silver Lake Guest Pool House Very Private !

The exterior of the villa features a charming design with a white picket fence surrounding well-maintained landscaping. Lush green grass and neatly trimmed shrubs complement the palm trees, while a clear blue sky provides a bright backdrop.