Family-friendly vacation rentals in Winter Garden

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Garden

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Kissimmee

4.92 out of 5 average rating, 133 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

Disney Playhouse – Your Dream Vacation Awaits! Indulge in elegance and comfort at this newly upgraded, pet-friendly retreat. Relax in your private pool & spa within a fully fenced backyard. Unwind in the plush master suite, enjoy Roku TVs in every room, and stay connected with blazing fast 1GB WiFi. The Diner Themed game room features a Marvel electronic pinball machine, pool table, and Wii. Pool heat is optional, hot tub always free! Pets welcome. King Master. Book your luxury getaway today!

Top guest favorite

A playground area features a yellow and brown slide, surrounded by swings and a textured gravel surface. Lush palm trees and colorful townhome buildings can be seen in the background, providing a bright and inviting recreational space.

Townhouse in Kissimmee

4.99 out of 5 average rating, 101 reviews

Family friendly/Pet friendly Orlando paradise

*PET AND CHILD FRIENDLY* *Long term renters welcome* 2 bedroom 2.5 bath Townhome in gated community! 10 mins to Disney, 20 to seaworld, and 30 to universal studios. Community includes large beautiful heated pool and playground/bbq area. Professional cleaning services after each guest stay. Fully stocked kitchen with Keurig coffee, all dishes, utensils, seasonings etc. All bathrooms fully stocked with toiletries and plenty of extra towels. Patio includes chairs, gas grill, and sitting area.

Superhost

A modern living space features a large sectional sofa with decorative pillows, positioned in front of a sleek entertainment center. The open-concept area includes a well-appointed kitchen with dark cabinets and a spacious island, illuminated by pendant lights.

Townhouse in Kissimmee

4.84 out of 5 average rating, 165 reviews

"The Haven" Newly Remodeled Luxury Townhome

This amazing townhome has recently been upgraded by the new owner to make it an even more impressive vacation rental. Over $20,000 was spent to upgrade beds, mattresses, all linen, towels, decor and many of the appliances. The home is completely modern and updated to impress any traveler to the area. The children will be wowed by the stunning Avengers loft/game room and the themed Toy Story and Harry Potter bedrooms. If all that wasn`t enough, the home is just 100 yards from the clubhouse.

Superhost

A luxurious cabana overlooks a sparkling pool, surrounded by palm trees and lounge chairs. A tray with drinks and snacks rests on a soft seating area, while the vibrant clubhouse is visible in the background, creating an inviting atmosphere for relaxation.

Townhouse in Kissimmee

4.88 out of 5 average rating, 125 reviews

Orlando Disney new House at Resort with lake view!

Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Superhost

Townhouse in Kissimmee

4.85 out of 5 average rating, 110 reviews

Amazing Home-Pool-Great Location-nr Disney & more

-Spacious updated 4 bedroom / 3 bath townhouse in a beautiful quiet resort - just 5 miles to DisneyWorld -Screened south-facing private pool, with the peace and quiet of the forest behind -Barely 2 minute walk to clubhouse, with 2 heated pools, hot tubs, cafe/bar and gym -Many shops and restaurants nearby -Flat screen TVs in living room and every bedroom -Newly updated well equipped kitchen -Washer & dryer -Free calls to Canada & US, WiFi, cable & high speed internet

Guest favorite

A colorful playground structure stands under shaded canopies, featuring climbing frames, a slide, and various activity panels. Surrounding palm trees and lush greenery enhance the outdoor setting, while safety surfacing cushions the play area.

Townhouse in Kissimmee

4.94 out of 5 average rating, 188 reviews

Beautiful family home near all attractions.

Beautiful, spacious and impeccable townhome close to all parks and entertainment with resort amenities. We follow Airbnb's enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights: *We sanitize high-touch surfaces, down to the doorknob. *We use cleaners and disinfectanst approved by global health agencies, and We wear protective gear to help prevent cross-contamination. *We clean each room using extensive cleaning checklist.

Guest favorite

A colorful playground features two blue slides and a yellow-roofed climbing structure, set among a bed of wood chips. The area is spacious, with RVs visible in the background, ensuring a family-friendly environment.

Cottage in Kissimmee

4.86 out of 5 average rating, 454 reviews

Yay! Cool Tiny Home Near All the Parks (98)

Located in the middle of it all. Hundreds of restaurants/shopping/grocery stores/pharmacies. You will love our great porch and the quiet atmosphere. One awesome thing about our neighborhood is that even though it is centrally located, you cannot hear any noise. 15 minutes from Disney, Sea World and Universal!! Deer, raccoons, and large water birds walk down the streets. Our cottage is great for families, couples, solo adventurers or business travel.

Guest favorite

Townhouse in Kissimmee

4.86 out of 5 average rating, 153 reviews

Peaceful & Clean Family Home near Disney & Airport

My place is good for couples & families with kids. Nice getaway resort with lots of extras. 3 Bedrooms, 2.5 Baths, with lovely Kitchen w/window and lots of light. Hot tub, iron table, washer and dryer. Closer walk to Pool/Amenity area. Very friendly place & very kid's oriented. 25 minutes from Disney, 30 Minutes from Universal and MCO International Airport. If you want to stay cool one day of no parks, this is the place to relax. Hablo Espanol...

Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 120 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

Is this home booked? We have more! Click on the circular profile image, then scroll down till you see James's Listings. Gated/24 hour security. Resort living with 2 main clubhouses and a few other extra quieter pools, playground and a soccer field. 10 min to Disney 15 min to Universal 10 min to the Convention Center Within a 5 min drive: Publix Grocery Walmart Target 10-15 restaurants

Superhost

Townhouse in Kissimmee

4.79 out of 5 average rating, 159 reviews

Resort Stay, Heated Pool, Water Slides and Hot Tub

Our lovely vacation home in the quiet community of Regal Oaks, is close to the theme parks and everything that Orlando has to offer for famiies with kids. Come relax at your own private spa after a long day at the parks, or enjoy the resort amenities, two water slides, two pools, a gym, and a tennis court; this is resort living with all the comforts of home.

Superhost

A spacious bathroom features dual sinks set in a dark granite countertop. Above, three light fixtures provide bright illumination. A clean, white shower curtain hangs in front of a bathtub, while a round mirror is positioned nearby, complementing the neutral color scheme.

Townhouse in Kissimmee

4.74 out of 5 average rating, 319 reviews

Sensory Friendly Villa

Ready for a relaxing, judgment-free getaway? Book my place and get ready to unwind! I'm thrilled you're thinking of my home, and I'm eager to earn your business! We've got some helpful hints for traveling with kiddos, and we'll even throw in free grocery delivery before you arrive via Shipt - no extra fee! Looking forward to hearing from you soon!