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Holiday rentals in Kissimmee

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Kissimmee

4.98 out of 5 average rating, 134 reviews

Runaway Beach Club Private Patio:Disney, Universal

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

11–18 Sep

₹10,797 per night
Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 501 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.

29 Dec – 5 Jan

₹5,667 per night
Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 164 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

1–8 May

₹9,069 per night

Popular amenities for Kissimmee holiday rentals

Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament346 locals recommend
Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend
Walmart Supercenter44 locals recommend

Other great holiday rentals in Kissimmee

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 364 reviews

Entire Cottage close to Disney, Universal, Airport

11–18 Jun

₹8,103 per night
Guest favourite

Home in Kissimmee

4.9 out of 5 average rating, 290 reviews

Family Home minutes from Disney!

13–20 May

₹9,816 per night
Guest favourite

Guest house in Kissimmee

4.93 out of 5 average rating, 135 reviews

Stylish guesthouse close to Disney

11–18 Aug

₹7,693 per night
Guest favourite

Tiny home in Kissimmee

4.94 out of 5 average rating, 326 reviews

Blue Bungalow Tiny House near all Attractions!!

10–17 Mar

₹8,883 per night
Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 204 reviews

3 bedroom Villa in Kissimmee

19–26 Mar

₹10,003 per night
Guest favourite

Tiny home in Kissimmee

4.9 out of 5 average rating, 433 reviews

ZMZ Tiny House Living! Try it out while at Disney

14–21 Jan

₹7,291 per night
Guest favourite

Tiny home in Kissimmee

4.95 out of 5 average rating, 142 reviews

Disney Tiny House Getaway!

29 Oct – 5 Nov

₹7,762 per night
Guest favourite

Guest suite in Kissimmee

4.94 out of 5 average rating, 119 reviews

Newly renovated near Disney and Universal Orlando

18–25 Feb

₹6,247 per night
Guest favourite

Guest house in Four Corners

4.98 out of 5 average rating, 420 reviews

Quiet Room Close to Disney and Attractions

31 Jul – 7 Aug

₹7,744 per night
Superhost

Cabin in Kissimmee

4.83 out of 5 average rating, 29 reviews

Romantic Cabin w/ Balcony + Tub + Hammock + Grill

11–18 May

₹9,621 per night
Superhost

Guest suite in Orlando

4.82 out of 5 average rating, 28 reviews

Beautiful Suite, with independent entrance parking

18–25 Dec

₹5,322 per night
Guest favourite

Guest house in Orlando

5.0 out of 5 average rating, 44 reviews

Guesthouse hosted by Yadier

17–24 Jun

₹9,339 per night

Quick stats about holiday rentals in Kissimmee

Total rentals

7.6T properties

Rentals with dedicated workspaces

3.9T properties have a dedicated workspace

Rentals with a pool

6.8T properties have a pool

Pet-friendly rentals

1.1T properties allow pets

Family-friendly rentals

6.6T properties are a good fit for families

Total number of reviews

2L reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee