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Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

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SUPERHOST
Entire condo · Kissimmee
Incredible Family Fun at Calypso Cay - 1 BR
Calypso Cay Resort is a family-friendly, Caribbean-themed Kissimmee property and is located famous for…Walt Disney World® Resort, Universal Studios® and Sea World®. The awesome amenities at Calypso Cay Resort include: 18 holes of mini golf, 3 outdoor heated pools, 2 are zero entry, 2 hot tubs, 3 water slides, License To Chill Tiki Bar & Grill, sand volleyball, lighted basketball, family grilling areas and covered cabanas, Dunkin’ Donuts, fitness room, game room, FREE WIFI and parking.
$61 per night
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SUPERHOST
Entire condo · Kissimmee
RESORT (02) NEAR DISNEY PARKS
Single apartment with all amenities, in excellent location, near DISNEY Parks, and many restaurants and shops, with access to major communication roads in the city
$99 per night
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SUPERHOST
Entire townhouse · Kissimmee
Disney World Vacation Home - The Mouse Townhouse #3
Stay at our Disney-inspired townhome just minutes from Disney World & steps from restaurants & stores. Your reservation will give you access to the resort’s amenities for up to 6 people without an additional charge! ✪AMENITIES✪ FantasyWorld amenities include: -Lazy river -Water slides -Heated pools -Pool bar -Splash pad -Jacuzzi -Gym -Picnic & BBQ areas -Playground -Arcade -Batting cages -Mini golf -Sports courts & more
$117 per night

Vacation rentals for every style

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Stay near Kissimmee's top sights

Photo of Kissimmee Lakefront Park
Kissimmee Lakefront Park38 locals recommend
Photo of Skate Reflections
Skate Reflections3 locals recommend
Photo of Medieval Times Dinner & Tournament
Medieval Times Dinner & Tournament97 locals recommend
Photo of Give Kids The World Village
Give Kids The World Village3 locals recommend
Photo of Silver Spurs Arena
Silver Spurs Arena3 locals recommend
Photo of Osceola Heritage Park
Osceola Heritage Park5 locals recommend

Houses in Kissimmee

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SUPERHOST
Entire home · Kissimmee
NEW LISTING: Heated Pool 15 Minutes to Disney
$251 per night
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SUPERHOST
Entire home · Kissimmee
3 bedroom Orlando Florida pool home
$100 per night
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SUPERHOST
Entire home · Kissimmee
South Facing Pool Home! 5 Miles from Disney
$158 per night
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Entire home · Kissimmee
5Bedrooms/5 Bathrooms Storey Lake (4777 KC)
$175 per night
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Entire home · Kissimmee
Beautiful Bright And Cozy 3•Bedroom🏡 Lovely Home
$139 per night
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Entire home · Kissimmee
BELLA VIDA 4575- 5 BEDROOMS - 12 GUESTS- GAME ROOM
$232 per night
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SUPERHOST
Entire home · Kissimmee
Modern 4 Bedroom House with Pool & Jacuzzi
$233 per night
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SUPERHOST
Entire home · Kissimmee
Private Heated Pool! Relax, Unwind and Enjoy!
$160 per night
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SUPERHOST
Private room · St. Cloud
Just a room. 30 miles to Disney. 40 miles to ocean
$28 per night
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SUPERHOST
Entire home · Kissimmee
4926 - Modern Home w/ Splash Pool
$142 per night
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SUPERHOST
Entire home · Kissimmee
3 bedroom Villa in Kissimmee
$90 per night
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Entire home · Kissimmee
Mickey's Crib, Kissimmee The Heart of Disney
$110 per night

Villa rentals in Kissimmee

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Entire villa · Kissimmee
Spacious Two Story 4-Bedroom Villa with Pool
$250 per night
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SUPERHOST
Entire villa · Kissimmee
Casa near Disney: 5 bed/3 bath lakefront pool home
$180 per night
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Entire villa · Kissimmee
Promotion Villa! Closed to Disney, Near Club House
$255 per night
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SUPERHOST
Entire villa · Kissimmee
Wizarding Enchanted Castle Lake View 6 BDRM Resort Villa 9mi to Disney 15mi to Wizarding World of Harry Potter
$149 per night
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Entire villa · Kissimmee
4815K Price
$270 per night
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Entire villa · Kissimmee
Modern, Newly Renovated Home w/ Pool near Disney
$212 per night
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Entire villa · Kissimmee
Villa near Disney 4Bd Luxury Villa Private pool
$150 per night
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Entire villa · Kissimmee
Fantasia @ Storey Lake by Shine Villas – #408
$214 per night
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SUPERHOST
Entire villa · Kissimmee
Private Heated Pool! Just 8 miles from Disney!
$182 per night
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Entire villa · Kissimmee
Luxury Villa near theme parks. FREE POOL HEATING.
$129 per night
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Entire villa · Kissimmee
Fantasy World Resort Vacation Villa Christmas Week
$175 per night
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Entire villa · Kissimmee
Blue Moon House - TOP Stay 10 Minutes from Disney
$217 per night

Weekly rentals in Kissimmee

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Entire home · Kissimmee
BELLA VIDA 4515MD - 4 BEDROOMS - 3 BATH - 8 GUESTS
$202 per night
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SUPERHOST
Private room · Kissimmee
Bedroom, private bath, vacation home near Disney 5
$55 per night
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SUPERHOST
Entire home · Kissimmee
Terra Verde 4B Home with Private Pool near Disney
$132 per night
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SUPERHOST
Entire home · Kissimmee
Recently Renovated 5 BR Home With Private Pool
$217 per night
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SUPERHOST
Private room · Kissimmee
Bedroom, private bath, vacation home near Disney 4
$51 per night
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SUPERHOST
Private room · Kissimmee
Comfortable and cozy room in Kissimmee
$38 per night
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Private room · Kissimmee
Very convenient place near Disney and airport
$37 per night
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Entire home · Kissimmee
Disney Magical Memories Vacation Home
$200 per night
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SUPERHOST
Entire home · Kissimmee
Amazing, Cozy 4BD/3BATH, DISNEY AREA, Private Pool
$154 per night
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Private room · Kissimmee
Private Bathroom & Close Airport,Park & Everything
$45 per night
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SUPERHOST
Private room · Kissimmee
Nice room with free parking included
$50 per night
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SUPERHOST
Private room · Kissimmee
Private Room in Orlando/Kissimmee (King 2)
$45 per night

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.


When is the best time to stay in a vacation rental in Kissimmee?

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.


What are the top things to do in Kissimmee?

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

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