Vacation Rentals in Kissimmee Area

$295 CAD
Per Night

Just inaugurated stunning 5bed 5bath pool home at Storey Lake
Villa Rental in Kissimmee, United States
5 Bedrooms · 14 Guests · #431015

$226 CAD
Per Night

Cypress Palms, the Ultimate Orlando Resort!
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426274

$239 CAD
Per Night

Cypress Palms, just miles from Orlando Studios!
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426273

$113 CAD
Per Night

Cypress Palms Has It All Near Disney!
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426272

$126 CAD
Per Night

Cypress Palms, the Perfect Family Getaway
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426271

$145 CAD
Per Night

Beautiful Star Island Resort in Florida
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426261

$239 CAD
Per Night

Stay at Star Island for Your Disney Getaway!
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426259

$103 CAD
Per Night

Discover the Magic of Disney with Star Island!
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426258

$145 CAD
Per Night

Star Island: A Perfect Paradise
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426256

$189 CAD
Per Night

Star Island: The Perfect Stay for Your Disney Trip
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426255

$251 CAD
Per Night

Visit Disney, Stay at Star Island!
Condo Rental in Kissimmee, United States
3 Bedrooms · 10 Guests · #426245

$145 CAD
Per Night

Experience the Magic of Disney with Star Island
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426244

$189 CAD
Per Night

Star Island: The Adventure Starts Here!
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426242

$170 CAD
Per Night

Cypress Palms in Gorgeous Orlando Florida!
Condo Rental in Kissimmee, United States
2 Bedrooms · 8 Guests · #426239

$132 CAD
Per Night

Enjoy Beautiful Cypress Palms in Florida!
Condo Rental in Kissimmee, United States
1 Bedroom · 4 Guests · #426238

$163 CAD
Per Night

Modern elegance with inspiring decor! Emerald Island 4/3 Townhome property - ten minutes to Disney!
Vacation Rental in KISSIMMEE, United States
4 Bedrooms · 8 Guests · #389007

$163 CAD
Per Night

Uniquely elegant Emerald Island 4/3.5 Townhome. Prestigious resort community ten minutes to Disney!
Vacation Rental in KISSIMMEE, United States
4 Bedrooms · 8 Guests · #389006

$151 CAD
Per Night

Emerald Island 3/2.5 Townhome full of upgrades. Resort community ten minutes from Disney! (CCL8424)
Vacation Rental in KISSIMMEE, United States
3 Bedrooms · 6 Guests · #389005

$151 CAD
Per Night

Modern, plush 3/2.5 Townhome property, fully furnished. Located ten minutes from Disney in Emerald I
Vacation Rental in KISSIMMEE, United States
3 Bedrooms · 6 Guests · #389004

$265 CAD
Per Night

Spacious Emerald Island 6/4 Pool Home with game room, spa, two master bedrooms with ensuite baths, t
Vacation Rental in KISSIMMEE, United States
6 Bedrooms · 12 Guests · #388861

$133 CAD
Per Night

Relaxing Home near Amusement Parks and Orlando Airport.
Vacation Rental in Kissimmee, United States
3 Bedrooms · 8 Guests · #388780

Save 5%


Sep 10 - Oct 20, 2017

$106 CAD
Per Night

Bella Vida Resort - 4571GALIE
Vacation Rental in Kissimmee, United States
3 Bedrooms · 6 Guests · #372911

$138 CAD
Per Night

Escape to a 4BR, 3BA Villa w/Recreation Room (151)
Villa Rental in Kissimmee, United States
4 Bedrooms · 8 Guests · #387291

$312 CAD
Per Night

Less than 8 miles from Disney! BV4564
Vacation Rental in Kissimmee, United States
6 Bedrooms · 12 Guests · #294071

$189 CAD
Per Night

Private Pool Home near Disney (3055)
Vacation Rental in Kissimmee, United States
4 Bedrooms · 12 Guests · #430225

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Kissimmee Area Vacation Rentals, Cottages & More!

Located in Central Florida along the shores of Lake Tohopekaliga, Kissimmee and its vacation rentals are just minutes from Orlando and its amusement parks, but offer more than just Mickey Mouse-themed attractions. 

At the Kissimmee Prairie Preserve State Park, more than 160 kilometres of trails allow hikers, bicyclists, and horseback riders to experience prairies, wetlands, and shady hammocks, in addition to Florida’s night sky (its remoteness makes it one of the state’s premier locations for stargazing). Lake Tohopekaliga provides some of the country’s best big bass fishing for anglers, and bird watchers will be well served with the ornithological opportunities on the Great Florida Birding Trail. 

Kissimmee’s historic downtown features a quaint waterfront, art exhibits, concerts, and live theatre performances. The city regularly hosts classic car shows, rodeos, and cattle auctions, as well as the annual Silver Spurs Festival—the largest rodeo east of the Mississippi, and a Kissimmee favourite since the 1940s. 

Kissimmee offers a vast array of natural and cultural attractions, as well as a variety of facilities and rental accommodation options, and is less than a thirty minutes’ drive from Orlando.

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