Family-friendly holiday rentals in The Villages

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.

4.92 out of 5 average rating, 13 reviews

Charming Villages Retreat

Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

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, 324 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, 150 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

Superhost

A charming treehouse sits elevated among large trees, connected by a wooden bridge. Surrounding space features a well-arranged outdoor sitting area with round wooden seating, and ample green grass is visible below, enhancing the natural setting.

Treehouse in Ocala

4.85 out of 5 average rating, 163 reviews

Woodpecker Treehouse Retreat

Take some time for yourself and enjoy the treehouse, you will marvel at nature, you will be surrounded by beautiful birds of different types, explore the place just 10 minutes from Santos Trailhead and 35 from Rainbow Springs. After you finish visiting Ocala and seeing its incredible recreational areas, enjoy our hot tub with hydro massage, relax in our hanging mesh, gather around the fire pit and make s'mores. Our Treehouse promises the perfect blend of nature's tranquility and modern comfort!

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, 153 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.

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, 58 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.

4.94 out of 5 average rating, 16 reviews

Outdoor Fun at the Pool + 2 Golf Carts!

Welcome to this POOL home with 2 GOLF CARTS! Spacious and inviting. UPGRADED WHITE cabinetry, extended DOUBLE PANTRY, GRANITE countertops. PLANTATION SHUTTERS. Featuring a large pool surrounded by an expansive deck and birdcage. Located near Spanish Springs Town Square and Lake Sumter Landing; Close to Tierra Del Sol Country Club and Championship Golf Course; Hacienda Championship Golf Courses, and Hacienda Regional Recreation Centers. No cats. Dogs under 20 lbs allowed with pet fee.

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!

4.84 out of 5 average rating, 103 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.

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.

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.

4.95 out of 5 average rating, 87 reviews

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

Your NEW home includes a very comfortable KING BED. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!!

Popular amenities for The Villages family-friendly rentals

Kitchen

Wi-Fi

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, 16 reviews

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

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, 49 reviews

Villages home with unique elevated front porch

4.93 out of 5 average rating, 125 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

A vibrant bedroom is showcased with a tropical-themed quilt featuring large leaf patterns in teal and white. A decorative pillow with a starfish design is positioned on a spacious bed, complemented by a nightstand adorned with a small decorative palm tree.

4.94 out of 5 average rating, 87 reviews

3 BR 2 BA Coastal-vibe,Golf Cart,Pools, Pickleball

4.98 out of 5 average rating, 142 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

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, 148 reviews

Modern Colonial+3 baths and Hot tub+ Pet Friendly

Family- and pet-friendly home rentals

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, 49 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

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, 18 reviews

Bay Breeze Villa

4.84 out of 5 average rating, 241 reviews

The exterior of the cottage showcases a covered patio area equipped with two wooden benches and a fire pit, set on a patterned stone surface. The surrounding yard features grass and trees, providing a peaceful outdoor space.

Cottage in Wildwood

Peaceful Cottage in the Heart of Wildwood

4.99 out of 5 average rating, 106 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, 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

4.95 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

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 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, 101 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

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, 23 reviews

The Mulligan House-The Villages

Superhost

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

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

A spacious screened lanai features comfortable seating arranged around a glass-top table. Outdoor dining spaces with a large umbrella and views of the fenced yard and greenery are visible in the background, providing a serene setting for relaxation.

5 out of 5 average rating, 5 reviews

Huge & luxurious home w/view of preserves & fenced

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, 46 reviews

Relaxing House in The Villages

5 out of 5 average rating, 24 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

A two-car garage is featured at the front of the villa, with a light-colored facade and green accents. The driveway is paved and flanked by neat landscaping, including palm trees and shrubs. Sunlight reflects off the building, creating a bright atmosphere.

5 out of 5 average rating, 10 reviews

Robin's Song in Brownwood

The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.