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
Apartment in Kissimmee
Close To Disney! 3 Bedroom Condo in Windsor Palms
Whatever your vacation style, our family-friendly 3 bedroom 2 bath top floor spacious condo, located in picturesque Windsor Palms gated community, will be waiting to welcome you home! Visit Disney World Attractions just 4.9 miles away, or grab a drink from the Tiki bar & relax by the pool. Whatever your style, this split bedroom privacy floor plan is perfect for traveling with family or friends. Equipped kitchen, free high-speed wifi, TVs in bedrooms, & more! *CLICK SHOW MORE FOR FULL DETAILS!*
25 Aug – 1 SeptIndividual Host,
£106 per night
4.96 out of 5 average rating, 138 reviews
Superhost
Apartment in Kissimmee
Beautiful Resort-Style Condo with Waterpark!
JJC Vacation Home is a gated resort-style condo that has everything you need to have the best vacation! The condo is near all main attractions, fully equipped kitchen, a lazy river, water slides, pool, splash area, mini golf, fitness center, kayak/canoe rental, bar, food, and more! Our Star Wars theme room with *glow in the dark* stars wall will make you feel like you're floating in space! Complimentary coffee/tea station. Relax while having a cup as you look at the view from the balcony.
15–22 OctIndividual Host,
£135 per night
4.85 out of 5 average rating, 153 reviews
Guest favourite
Apartment in Kissimmee
First floor/your Disney escape
Our condo is located on the first Floor at resort-style community (with No Resort FEES and FREE parking) with a nice clubhouse featuring a game room, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.
14–21 SeptIndividual Host,
£99 per night
4.92 out of 5 average rating, 110 reviews

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
Tiny home in Orlando
The Little Treehouse 2 at Country Club of Orlando
1–8 OctIndividual Host,
£117 per night
4.98 out of 5 average rating, 624 reviews
Guest favourite
Cabin in Davenport
$89! Cozy Cabin- Disney 20 Miles Away!
25 May – 1 JunIndividual Host,
£100 per night
4.92 out of 5 average rating, 163 reviews
Guest favourite
Guest suite in Kissimmee
Newly renovated near Disney and Universal Orlando
22–29 AprIndividual Host,
£71 per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
17–24 May
£110 per night
4.92 out of 5 average rating, 164 reviews
Superhost
Home in Kissimmee
3 bedroom Orlando Florida pool home
5–12 NovProfessional Host,
£114 per night
4.78 out of 5 average rating, 253 reviews
Guest favourite
Cottage in Davenport
$79! Cozy Cottage + Outdoor Fun -Close to Disney!
10–17 May
£90 per night
4.92 out of 5 average rating, 122 reviews
Superhost
Apartment in Kissimmee
2BD/2BA Storey Lake condo close to Disney #51
2–9 SeptProfessional Host,
£140 per night
4.79 out of 5 average rating, 204 reviews
Guest favourite
Tiny home in Kissimmee
Disney Tiny House Getaway!
10–17 Nov
£88 per night
4.95 out of 5 average rating, 141 reviews
Guest favourite
Tiny home in Kissimmee
Luxury Tiny Cottage. Only 5 miles from Disney!
28 Aug – 4 SeptIndividual Host,
£95 per night
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in Kissimmee
20min to Disney/Free Parking/Gym/Pool/Gated
27 May – 3 Jun
£101 per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Guest house in Orlando
Guesthouse hosted by Yadier
19–26 May
£113 per night
5.0 out of 5 average rating, 43 reviews
Guest favourite
Townhouse in Kissimmee
Summer Studio at Kissimmee
1–8 Aug
£79 per night
5.0 out of 5 average rating, 9 reviews

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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