
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.

2/2 custom pool home with 4 person gas golf cart
Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

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.

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.

Walk to Sumter w/cart - Beautiful Courtyard Villa
We love this home because the location is FANTASTIC! It's under a mile to Sumter Landing (walking distance for us :)). Also, new floors, paint, etc! The living room furniture is extremely comfortable! The kitchen has everything you need. The beds are comfortable and there is a tv in every room. (The second bedroom but needs your own Roku or Firestick!) There is a cart included which is the best way to see The Villages. We know you will love it here! Let us know if you have any questions.

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.

2/2 Villa in Citrus Grove - Rates Reduced!
*Redone in 2023* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

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!

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.

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.

VIEW-T-FUL! w/Golf cart
Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

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.

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
Family-friendly home rentals with a hot tub

Pet Friendly, Modern Tiny Home in Clermont!

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

Villages home with unique elevated front porch

Spacious Bungalow with Private Pool and Courtyard

Pool + Heated spa Family friendly King suite Oasis

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

Cozy 2 bedroom home near The Villages

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

Beautiful House On the River, Kayaks, Large Dock!

Heated Pool Golf Cart Dog Friendly in The Villages

Peace and Quiet
Family-friendly home rentals with a pool

Villa la Bella

Poolside Palms in The Villages, Florida

Spacious 3BR in The Villages | King Bed | Golfcart

The Mulligan House-The Villages

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

Huge & luxurious home w/view of preserves & fenced

New home in the new part of the villages.

The Sunshine Retreat with Golf Car
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
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- Family-friendly rentals Marion County
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- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Weeki Wachee Springs
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Rainbow Springs State Park
- Fort Island Beach
- Universal's Islands of Adventure
- Shingle Creek Golf Club
- Crayola Experience
- Fun Spot America