
Family-friendly holiday rentals in The Villages
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in The Villages
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

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

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.

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.

New Luxury Home-Pool-Waterfront View-3 King Suites
Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

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!

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.

Cozy A-Frame Retreat w/ hot tub!
Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

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.

New home in the new part of the villages.
Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

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!!

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 The Villages family-friendly rentals
Family-friendly home rentals with a hot tub

Pet Friendly, Modern Tiny Home in Clermont!

Villages home with unique elevated front porch

Spacious Bungalow with Private Pool and Courtyard

Pool + Heated spa Family friendly King suite Oasis

Welcome to the Villages

Modern Colonial+3 baths and Hot tub+ Pet Friendly

Log cabin on the river

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages
Family- and pet-friendly home rentals

Pool Home Great Location 3/2 & 2 Golf Carts

Peaceful Cottage in the Heart of Wildwood

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

Getaway on the Waterway: Kayak, SUP, fish, relax!

Family Tides 3 Richmond

Heated Pool Golf Cart Dog Friendly in The Villages

Peace and Quiet

The Villages, Heated Pool Walk to Sawgrass
Family-friendly home rentals with a pool

Villa la Bella

Poolside Palms in The Villages, Florida

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

Sapphire Cottage - sleeps 6, on 5 acres with canal

Robin's Song in Brownwood

The Villages, Citrus Grove home away from home

Silver Lake Guest Pool House Very Private !

Great location and reviews! Free Golf Cart!
Quick stats about holiday rentals that are family-friendly in The Villages
Total rentals
720 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
13K reviews
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
280 properties have a pool
Rentals with dedicated workspaces
430 properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Destin Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Panama City Beach Holiday rentals
- Pet-friendly rentals The Villages
- House rentals The Villages
- Rentals with breakfast The Villages
- Waterfront rentals The Villages
- Apartment rentals The Villages
- Rentals with a washing machine and dryer The Villages
- Rentals with lake access The Villages
- Fitness-friendly rentals The Villages
- Rentals with a patio The Villages
- Villa rentals The Villages
- Rentals with a fireplace The Villages
- Cottage rentals The Villages
- Rentals with a firepit The Villages
- Rentals with pools The Villages
- Rentals with a hot tub The Villages
- Rentals with outdoor seating The Villages
- Flat rentals The Villages
- Family-friendly rentals Marion County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Weeki Wachee Springs
- Disney Springs
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Aquatica
- Walt Disney World Resort Golf
- Island H2O Water Park
- Rainbow Springs State Park
- Disney's Hollywood Studios
- Universal CityWalk
- ICON Park
- Universal's Islands of Adventure
- Fort Island Beach
- Crayola Experience
- Shingle Creek Golf Club