Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

Guest favorite
Guest suite in Kissimmee
Newly renovated near Disney and Universal Orlando
Entire suite , new ultra comfortable king size bed, free wifi, 64"TV with Netflix and Amazon Prime. Private bath, Living room and kitchen, shared laundry room, free parking 13 miles or 21 minutes from Disney World, Disney Springs shops and restaurants and Orlando Premium Outlets 16.6 miles or 23 minutes from Universal Orlando. 12.6 miles or 22 minutes from Aquatica and SeaWorld Orlando 11.6 miles or 22 minutes from Orlando International Airport 15 miles or 25 minutes from the Convention Center
Oct 3 – 10
$62 per night
4.94 out of 5 average rating, 117 reviews
Guest favorite
Townhouse in Kissimmee
Beautiful Townhouse Near Disney! Private Hot Tub!
Welcome! This beautiful 2bd/2.5 bath townhouse is just 15 minutes from Disney! Our prime location is also close to other central Florida attractions such as Universal Studios and SeaWorld! There is a private hot tub in the backyard patio to enjoy after a long day at the parks! We also provide travel-sized toiletries, fresh towels, laundry supplies, etc., so you can pack light! We know that traveling can be tiring so please allow us to offer you an amazing home away from home. Happy travels!
Jan 6 – 13
$117 per night
4.89 out of 5 average rating, 141 reviews
Guest favorite
Home in Kissimmee
3 bedroom Villa in Kissimmee
The villa is in a quiet residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.
Feb 14 – 21
$103 per night
4.84 out of 5 average rating, 203 reviews

Popular amenities for Kissimmee vacation 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 vacation rentals in Kissimmee

Guest favorite
Townhouse in Kissimmee
Luxurious Dream 4/3 Bedroom Home w/private Pool
Oct 11 – 18
$167 per night
4.87 out of 5 average rating, 122 reviews
Condo in Kissimmee
Beautiful Resort-Style Condo with Waterpark!
Sep 30 – Oct 7
$126 per night
4.85 out of 5 average rating, 152 reviews
Guest favorite
Condo in Kissimmee
BRAND NEW CONDO- 2 BR 2 Bath-Great location!
Feb 7 – 14
$119 per night
4.95 out of 5 average rating, 171 reviews
Guest favorite
Cottage in Kissimmee
2/2 Condo with Private Patio:Disney, Pet Friendly
Oct 18 – 25
$122 per night
4.98 out of 5 average rating, 132 reviews
Guest favorite
Home in Kissimmee
Windsor Orlando Private Arcades,Theater,Pool-Spa
Aug 16 – 23
$375 per night
5.0 out of 5 average rating, 167 reviews
Guest favorite
Guesthouse in Orlando
Livingston Pool House- In The Heart of Downtown
Oct 25 – Nov 1
$173 per night
4.99 out of 5 average rating, 189 reviews
Guest favorite
Condo in Kissimmee
2BD/2BA condo close to Disney at Storey Lake #96
Oct 25 – Nov 1
$137 per night
4.88 out of 5 average rating, 128 reviews
Home in Kissimmee
3 bedroom Orlando Florida pool home
Nov 6 – 13
$105 per night
4.78 out of 5 average rating, 251 reviews
Guest favorite
Guest suite in Kissimmee
Little Blue House with private entrance & parking
Feb 10 – 17
$76 per night
4.98 out of 5 average rating, 153 reviews
Guest favorite
Townhouse in Kissimmee
Resort-style home close to Disney with jacuzzi
Aug 31 – Sep 7
$136 per night
4.97 out of 5 average rating, 168 reviews
Guest favorite
Guest suite in Orlando
Location, Location, Location near all attractions
Sep 2 – 9
$127 per night
4.99 out of 5 average rating, 235 reviews
Townhouse in Kissimmee
Oct 6 – 12
$89 per night
4.82 out of 5 average rating, 137 reviews

Quick stats about vacation 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

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.

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.

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.

Destinations to explore

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