Family-friendly holiday rentals in The Villages

5 out of 5 average rating, 21 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.

Flat 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, 330 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, 158 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 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, 175 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, 126 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, 138 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!

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, 104 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!

4.85 out of 5 average rating, 112 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, 101 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.

4.97 out of 5 average rating, 176 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.

The exterior of the home showcases a well-manicured lawn with vibrant landscaping. Palm trees and shrubs frame the entrance, while a driveway leads to the two-car garage. The home features a charming façade, complemented by a clear blue sky above.

4.88 out of 5 average rating, 56 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

This stunning designer home comes with a golf cart and is within walking distance to Lake Sumter Market Square. It sleeps 4 adults in 2 bedrooms. 5G Wi-Fi. Kitchen is loaded with amenities & spices, lots of comfy lounging spaces, an inside laundry room, 2-car garage, landscaped yard and easy access to Hwy 466. 3-day min. May-Sep, 7-night min. Oct, Monthly stays only Nov-Apr. You will love staying in this stylish home away from home.

4.97 out of 5 average rating, 362 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.

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

4.94 out of 5 average rating, 109 reviews

Tiny home in Clermont

Pet Friendly, Modern Tiny Home in Clermont!

5 out of 5 average rating, 55 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

4.93 out of 5 average rating, 132 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, 148 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.

4.95 out of 5 average rating, 19 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

4.88 out of 5 average rating, 156 reviews

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, 179 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

A decorative sign is mounted on the wall, featuring a blue background with white text that reads 'welcome to our happy place.' The sign is framed in a simple wooden border, adding a homey touch to the interior.

4.8 out of 5 average rating, 106 reviews

Carlton Courtyard Villa - Walk to Sumter Landing

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, 22 reviews

Bay Breeze Villa

4.84 out of 5 average rating, 245 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

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, 139 reviews

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

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.

5 out of 5 average rating, 17 reviews

Family Tides 3 Richmond

4.96 out of 5 average rating, 91 reviews

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

5 out of 5 average rating, 34 reviews

A relaxing outdoor space features a circular seating area with bright green chairs surrounding a fire pit. A stack of firewood is placed nearby, with twinkling string lights overhead. In the background, a dining area and a hot tub can be seen within a spacious yard.

Farm stay in Webster

Welcome happy Campers, have fun!

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.

4.91 out of 5 average rating, 33 reviews

Ideal location! 3/2 Stetson model w/4 man golfcart

Family-friendly home rentals with a pool

Superhost

An inviting outdoor space features a cozy seating area with a modern sofa and a coffee table. A sleek electric fireplace is mounted on a stone wall, accompanied by a wall-mounted TV. The private pool reflects the surrounding palm trees, while patio furniture creates an atmosphere for relaxation.

4.8 out of 5 average rating, 5 reviews

Poolside Palms-w/ Pool & Golf Cart in The Villages

5 out of 5 average rating, 28 reviews

The Palms. Luxurious, giant pool, golf, pond view

A large outdoor pool is surrounded by a spacious deck, featuring neatly arranged lounge chairs. Palm trees are visible in the background, and a covered area with seating can be seen to the left. The sky features a mix of soft blue and wispy clouds.

5 out of 5 average rating, 8 reviews

2 min walk to pool, 4 seat cart, 5 min to Eastport

4.98 out of 5 average rating, 50 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

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.

4.97 out of 5 average rating, 29 reviews

Brownwood Square - Villages Home

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.

4.97 out of 5 average rating, 68 reviews

Newer Villa in The Villages near Brownwood

A private outdoor area features a heated pool and spa, surrounded by screen enclosure. Comfortable seating is arranged beside the pool, complemented by an outdoor dining setup. The space is designed for relaxation with a stylish stone paver patio and clear blue skies above.

4.92 out of 5 average rating, 12 reviews

Pool and Spa Luxury Retreat

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.