Discover Vacation rentals in Kissimmee, Florida
Find amazing vacation homes from cabins, villas, cottages in Kissimmee
Explore the Wonders of Kissimmee
Coined as the ‘Vacation home capital of the world, Kissimmee takes the title for being the largest city and the County seat of Osceola, Florida. The city boasts an area of 17.32 square miles with 16.7 square miles taking up the land and 0.6 square miles of water. Before the Europeans settled in, the land was owned by a native American tribe called the Jororo, which meant ‘long water’ in the Jororo language.
Explore Vacation Homes
3BR Luxury country-side cottage
$2,725.00 per night
10BR Beachfront Villa for Parties
$1,850.00 per night
Cozy Cabin with Private Pool
$1,500.00 per night
7BR Sea-View Vacation Home
$2,250.00 per night
2BR Luxury contemporary house
$3,250.00 per night
12BR Farmhouse House for Party
$750.00 per night
Lakefront Cottage in the woods
$950.00 per night
Guest Cottage Deckview + Pool
$2,950.00 per night
Tropical Oasis- 6 Private Rooms
$1,550.00 per night
5BR Big Boulder Lake Vacation Home With Mountain Views (10)
5BR Lakefront Home Rental in Lake Harmony Poconos (34S)
4BR Lake House for Rent with Kayak & Dock in Poconos (36s)
Farmhouse Rentals with Barn for Wedding Getaways – Poconos (1735)
Mesmerising Villa/Castle for Rent with Indoor Pool in Poconos, PA (252)
174 Acre Luxury Mansion Rental with Private Pool in Poconos – PA (1700)
“As a family from the northeast, we were looking for a warm, sunny vacation destination and Kissimmee fit the bill perfectly. We stayed in this lovely cottage, which was close to Disney World and other attractions, but also quiet and peaceful. The cottage was charming and well-equipped, and we had a wonderful time. We would definitely stay here again!”
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Embark your Weekend Getaway
Kissimmee does a number on you when it comes to spending your vacation. You have options of exploring the urban jungle of one of the famous tourist spots, nature retreats of safari, the pioneer village, airboat tours, and much more. You can also embark on ‘off-road adventures to traverse the muddy terrain to bring out the adrenaline junkie in you. If being a green thumb is your quirk, you can explore the allure of the natural gardens and bird sanctuaries for the traveler you’re all about.
Reasons to book with us
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Kissimmee, Florida is located in central Florida, just south of Orlando. To get there, you can fly into Orlando International Airport and then take a rental car or ride-sharing service to Kissimmee.
Kissimmee is very close to Disney World and other theme parks. In fact, many vacation home rentals in Kissimmee are located within a short drive of the parks.Its around 15 Min car ride.
In addition to the theme parks, Kissimmee has many fun things to do, including outdoor activities like hiking, biking, and fishing, as well as shopping, dining, and entertainment options. Some popular attractions in Kissimmee include Old Town, a nostalgic amusement park and shopping district, and the Kissimmee Lakefront Park, which offers beautiful views of Lake Tohopekaliga.
Kissimmee hosts many special events and festivals throughout the year, including the Osceola County Fair and the Annual Food and Wine Celebration. You can check the local events calendar to find out what’s happening during your visit.
Our company founders began renting out their two vacation homes in 2017. They started welcoming guests, envisioning a new set of hospitality ideas for a luxurious and comforting experience. Today, Holiday Keepers has multiple properties in different cities.
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