Family-friendly holiday rentals in Osceola County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Osceola County

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

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Guest favourite

Townhouse in Kissimmee

4.97 out of 5 average rating, 280 reviews

Find a Little Magic in a Townhouse near Disney and Universal

This is a 1500 sq ft townhouse located behind the area of Old Town off of US hwy 192 and just minutes from the Disney resort area. The space includes a screened in patio with hot tub and relaxation area which might come in handy after your long day at the parks. The patio faces a wooded area, offering additional seclusion and privacy. As part of the Regal Oaks community, our guests have access to a beautiful community swimming pool, gym, and clubhouse restaurant. This is also a gated community which provides added security and sense of mind for your time away from home. There are many similar listings in this area, however, as our guest we can guarantee an exceptionally clean home that is both inviting and luxurious and an unforgettable Airbnb experience for the same competitive price. Guests are able to access the entire house with the exception of the AC/utility closet in the upstairs guest bathroom and the two storage closets downstairs which are all equipped with locks. Our interaction with guests is generally hands-off unless a situation arises in which our guests need assistance in any way. It's a skip and a hop to the Disney Resort and Universal from this home. Kids will also love the shared amenities at the Regal Oaks gated vacation community. Stores and more restaurants can be found a short walk away in nearby Old Town. Unfortunately, public transportation in the Kissimmee area in general is poor. The best way to get to and from any destination outside of the community is with a rental car or ride sharing service. The community does however, offer an excess of free parking throughout. We have not had many noise complaints in the past however as this is a vacation community with high guest turnover, the potential for loud neighbors is possible but unlikely.

14–21 Dec

$380 NZD per night

Guest favourite

Cottage in Kissimmee

4.9 out of 5 average rating, 210 reviews

Be Our Guest Sandcastle Cottage 81

Located-Encore Tropical Palms RV Resort 5 min to Disney property and minutes away from various restaurants. Old Town and Fun Spot are right next to the property. New renovated floors just installed! (May 2023) Has private bedroom with queen bed and upstairs loft with 2 twin beds for the kids. Newer sofa and recliner and washer/dryer. Stainless Steel Appliances and granite tile counter tops in kitchen. Smart TV in living room. Resort style pool with kiddie area. Miniature Golf area. Free WiFi

23–30 Oct

$201 NZD per night

Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 513 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers, we offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We are happy to continue offering our apartment with a 5-star cleanliness rating. We offer our home to travelers only-we do not accept local reservations.

17–24 Jan

$141 NZD per night

Guest favourite

Cottage in Lake Wales

4.88 out of 5 average rating, 108 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

10–17 Mar

$267 NZD per night

Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

21–28 Apr

$256 NZD per night

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

A full cottage for 4! The perfect place stay. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check out unit We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

30 Jul – 6 Aug

$206 NZD per night

Guest favourite

Tiny home in Kissimmee

4.94 out of 5 average rating, 328 reviews

Blue Bungalow Tiny House near all Attractions!!

Our Tiny House in Mill Creek RV Resort is minutes away from Disney, Universal, Sea World & most area attractions. Our cozy cottage has a private bedroom, full kitchen, large island, living room, bathroom, free washer/dryer, and the perfect front porch. There is a private drive and free parking. The resort is peaceful with plenty of amenities! We have four tiny house cottages - please check us out on Facebook under Tiny Mouse Houses to find the Airbnb links.

28 Oct – 4 Nov

$210 NZD per night

Guest favourite

Guest suite in Kissimmee

4.86 out of 5 average rating, 567 reviews

Private Studio in POOL home

Hello! We offer a portion of our home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the apartment with access to Prime. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio with a 5-star cleanliness rating.

7–14 Jul

$155 NZD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 790 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; meemaws-country -cottage which sleeps six.

21–28 Apr

$330 NZD per night

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 227 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

18–23 Sep

$255 NZD per night

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 142 reviews

KISSIMMEE VACATION HOME NEAR ALL ATTRACTIONS

Comfortable apartment in a centralized location. The apartment is not in a gated community. This location is 10 miles from Orlando International Airport, 13 miles from the welcome entrance to Disney, 18 miles to Universal and 13 miles to SeaWorld. We are 7 miles from Gatorland Theme Park and 15 miles to International Dr. Traffic during the day could play a big part in travel times, but there are a few alternate toll routes available.

11–18 May

$231 NZD per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

17–24 Sep

$201 NZD per night