Family-friendly vacation rentals in 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

4.92 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, 121 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!

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

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, 97 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!

4.96 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.

Superhost

5 out of 5 average rating, 3 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.

4.97 out of 5 average rating, 354 reviews

A wooden door with a pointed roof stands surrounded by lush green foliage. The door features two windows with sheer curtains, providing a glimpse of the natural surroundings, while a stone pathway leads up to it, enhancing the inviting entrance.

Farm stay in Ocala

Tiny Hobbit cabin on lovely Fort Brook Horse Farm

Hi everyone! This little cabin is a bedroom with a queen size bed. It is camping. It includes coffee maker,pods Cream , Sugar. It has a/c electricity and a lamp. The restroom and showers are Close by. You have a fire pit that is a grill and table and chairs just out front. You might want to grab some wood and match light charcoal makes cooking on the grill easier. You are welcome to pet the horses and goats. Louie the dog is friendly too.

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

Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.

Popular amenities for The Villages family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

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 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!

A screened-in outdoor area features a sparkling pool surrounded by inviting lounge chairs and a dining table. Lush greenery and colorful decor contribute to a serene atmosphere, while the clear sky and soft clouds create a bright ambiance.

4.86 out of 5 average rating, 21 reviews

Heated Pool, Dog Friendly, Golf Cart Included

4.95 out of 5 average rating, 22 reviews

Spotless Villa Near Brownwood Sq- Lanai & King Ste

5 out of 5 average rating, 15 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

4.98 out of 5 average rating, 47 reviews

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.

Home in Lady Lake

Relaxing House in The Villages

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!

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

Family-friendly home rentals with air conditioning

The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.

5 out of 5 average rating, 13 reviews

Designer Home in The Villages, FL.

5 out of 5 average rating, 50 reviews

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.

Home in Lady Lake

Villages home with unique elevated front porch

A spacious living area is presented, featuring a light-colored sofa paired with white accent tables. A ceiling fan above enhances airflow, and modern kitchen appliances are visible in the background. Natural light floods the space, highlighting the hardwood flooring and simple decorative touches.

5 out of 5 average rating, 19 reviews

Bay Breeze Villa

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

5 out of 5 average rating, 47 reviews

The exterior of a villa is showcased at dusk, featuring a well-maintained landscape with palm trees and shrubs. A two-car driveway leads to a garage, with soft lighting illuminating the entrance. The sky reflects pink and purple hues overhead.

Villa in The Villages

Palm Oasis Retreat - Dog Friendly w/golf cart

A modern living area is showcased with light gray sofas and a wood coffee table. Decorative cushions in various shades add pops of color. Natural light enters through two windows, complemented by sheer curtains. A patterned area rug lies beneath, enhancing the space's cozy feel.

4.98 out of 5 average rating, 41 reviews

Cozy Patio Villa (Newell)

4.97 out of 5 average rating, 61 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

A single-story home is showcased with a well-maintained front yard, featuring manicured grass and small landscaping elements. The exterior is designed with a light-colored facade, and large windows reflect the evening sky's hues. A two-car garage is included, along with a spacious driveway.

5 out of 5 average rating, 24 reviews

BrandX Premium - 1921 McMurtrie

Family-friendly home rentals with Wifi

A single-story villa is surrounded by a white picket fence and lush landscaping. The large covered patio features seating, offering a shaded area to relax. Nearby homes are visible, set amid a clear blue sky dotted with fluffy clouds.

4.97 out of 5 average rating, 29 reviews

You’ve Arrived! Stunning Home in the Villages!

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.

4.96 out of 5 average rating, 47 reviews

Beautifully Furnished 3/2 with In-ground Pool

A stylish living area features a combination of leather and upholstered seating, arranged around a circular coffee table. Natural light pours in through large windows, complemented by decorative plants. A geometric rug anchors the space, providing a cozy atmosphere for gatherings.

5 out of 5 average rating, 9 reviews

Sumter Landing Oasis / Golf Cart

A single-story home is seen with a light gray exterior, framed by a large tree in the front yard. An American flag is displayed on the porch, and a white truck is parked in the driveway. Lush green grass surrounds the house.

5 out of 5 average rating, 10 reviews

perfectly located Villages home

The exterior of a modern villa is depicted, showcasing a light-coloured facade with a two-car garage. A white picket fence encircles manicured shrubs and grass. The front porch is partially visible, with large windows inviting natural light.

5 out of 5 average rating, 15 reviews

Blue Sky Villa, Your Home Away From Home.

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, 97 reviews

Fabulous Courtyard Villa close to Sumter Landing

4.95 out of 5 average rating, 22 reviews

A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.

Home in Wildwood

Brownwood Square - Villages Home

A single-story home is surrounded by lush green grass and palm trees. The driveway features smooth concrete, leading up to a spacious garage with modern glass doors. Soft clouds drift in a pastel sky, providing a serene backdrop to the property.