
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

Luxury Pool Home with a View in The Villages, FL
Enjoy your own private sports pool, spa, and climate-controlled lanai as well as all of the amenities that The Villages has to offer. Free executive golf courses, water volleyball, and water aerobics for stays of 30+ days. Pickleball, tennis, billiards, shuffleboard, bocce ball, outdoor exercise equipment and nightly entertainment for all guests. Get to Brownwood town square in approximately 10 minutes. This home is located on a pond with a natural preserve beyond the pond. No garage access.

Virginia Trace | 1 mile to square, walk to pool
1 mile from Lake Sumter Town Square Virginia Trace Villa has everything you need in this updated 3 BR, 2 bath 1740 sq ft villa. A perfect space centrally located to explore The Villages. The villa features a spacious LR area w/ a 65" smart TV, fully stocked kitchen, 2 dining areas, & screened in patio where guests can relax & enjoy the sitting area. In unit washer & dryer. Wifi & parking included. Golf cart accessible. Guest passes available upon request (provide info 3 days prior to check-in).

Whole House-sleeps 10 The Villages Spanish Springs
Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

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

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!

Pirates & Parrots - The Villages - Golf Cart &Pool
GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

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.

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.

Perfect "get-away" home for a couple or family!
Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. I offer a golf cart for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

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!
Popular amenities for The Villages family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Tiny Home in Clermont, No Pet Fees

5-Star Luxury | Prime Location & Top Amenities

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

Spacious Bungalow with Pool and Courtyard

Pool + Heated spa Family friendly King suite Oasis

Villages 3/2 with Golf Cart and Hot Tub

Welcome to the Villages

3 bdrm 2 ba fully furnished!
Family- and pet-friendly home rentals

StJohns is a great area for golf, hiking, Kayaking

Seashell Villa~Pet Friendly~Golf Cart

Briar Meadow Villa - Dogs are welcome!

Cute & Cozy Tiny Guesthouse

Charming Villages Retreat

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Luxury Villages Stay • Golf Cart • Near Brownwood

Home away from home entire house
Family-friendly home rentals with a pool

Villa la Bella

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

Get it all - Pool, Jacuzzi, Golf View, & Golf Cart

King Bed, Golf Cart, Small Dogs & Water Filter!

Home with private pool, Tierra grande villas

Newer Villa in The Villages near Brownwood

The Villages pool property with a 4-person cart!

The Villages, Citrus Grove home away from home
When is the best time to visit The Villages?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $227 SGD | $255 SGD | $245 SGD | $169 SGD | $151 SGD | $140 SGD | $133 SGD | $129 SGD | $134 SGD | $151 SGD | $171 SGD | $188 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about holiday rentals that are family-friendly in The Villages

Total holiday rentals
Explore 790 holiday rentals in The Villages

Nightly prices starting at
The Villages holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 14,640 verified reviews to help you choose

Pet-friendly holiday rentals
Find 330 rentals that welcome pets

Holiday rentals with a pool
310 properties feature pools

Rentals with dedicated workspaces
510 properties have a dedicated workspace

Wifi availability
790 of The Villages holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across The Villages rentals

4.9 Average rating
The Villages stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Family-friendly rentals Marion County
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- Family-friendly rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Weeki Wachee Springs
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Rainbow Springs State Park
- ESPN Wide World of Sports
- Universal's Islands of Adventure
- Shingle Creek Golf Club
- Ocala National Forest





