Holiday rentals in Kissimmee

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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 Sept

£121 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.

18–25 Nov

£110 per night
Guest favourite

Flat in Kissimmee

4.92 out of 5 average rating, 200 reviews

Modern APT W/ Patio 15 mins from Theme Parks & MCO

Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado

6–13 Jun

£112 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

Apartment in Kissimmee

4.98 out of 5 average rating, 283 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

22–29 Aug

£120 per night
Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 204 reviews

3 bedroom Villa in Kissimmee

23–30 Sept

£119 per night
Guest favourite

Apartment in Kissimmee

4.91 out of 5 average rating, 111 reviews

First floor/your Disney escape

18–25 Sept

£105 per night
Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 364 reviews

Entire Cottage close to Disney, Universal, Airport

11–18 Jun

£97 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

18–25 Sept

£85 per night
Guest favourite

Holiday home in Orlando

4.82 out of 5 average rating, 100 reviews

The Lovers Haven (Romantic Studio w/ Balcony)

12–19 Sept

£107 per night
Guest favourite

Guest house in Kissimmee

4.93 out of 5 average rating, 135 reviews

Stylish guesthouse close to Disney

2–9 Jul

£94 per night
Guest favourite

Tiny home in Kissimmee

4.95 out of 5 average rating, 142 reviews

Disney Tiny House Getaway!

29 Apr – 6 May

£87 per night
Guest favourite

Apartment in Kissimmee

4.88 out of 5 average rating, 48 reviews

Stylish Condo 20 mins to Disney/King Bed

26 Sept – 3 Oct

£107 per night
Guest favourite

Townhouse in Kissimmee

5.0 out of 5 average rating, 9 reviews

Summer Studio at Kissimmee

12–19 Sept

£79 per night
Guest favourite

Guest house in Orlando

5.0 out of 5 average rating, 44 reviews

Guesthouse hosted by Yadier

29 May – 5 Jun

£107 per night
Guest favourite

Apartment in Kissimmee

5.0 out of 5 average rating, 7 reviews

Resort Oasis Near Disney World

29 Sept – 6 Oct

£114 per night

Quick stats about holiday rentals in Kissimmee

Total rentals

7.6K properties

Rentals with dedicated workspaces

3.9K properties have a dedicated workspace

Rentals with a pool

6.8K properties have a pool

Pet-friendly rentals

1.1K properties allow pets

Family-friendly rentals

6.6K properties are a good fit for families

Total number of reviews

197K reviews

Your guide to Kissimmee

All about Kissimmee

Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.


The best time to stay in a holiday rental in Kissimmee

The weather in central Florida is nice year-round — there’s a reason it’s called the Sunshine State. Winters in Kissimmee tend to be sunny, warm, and dry, so around the holidays, Florida tends to be a popular escape for those who live in colder climates. Though temperatures hover around 70 degrees Fahrenheit from December through February, you’ll still want to pack a jacket. In the busy summer months, you can expect temperatures around 90 degrees and the kind of humidity that makes air conditioning a necessity. Keep in mind that summer and early autumn also bring hurricanes to Florida. Spring and fall can be considered the best of both worlds, with lovely weather and fewer crowds, ideal seasons to stay in one of the area’s villas.


Top things to do in Kissimmee

Old Town

Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.

Fan Boat Swamp Tour

Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.

Hot Air Balloon Ride

Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.

Destinations to explore

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