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

35+ 8 9


$2,725.00 per night

10BR Beachfront Villa for Parties

25+ 12 7


$1,850.00 per night

Cozy Cabin with Private Pool

42+ 20 7


$1,500.00 per night

7BR Sea-View Vacation Home

18+ 10 5


$2,250.00 per night

2BR Luxury contemporary house

25+ 20 16


$3,250.00 per night

12BR Farmhouse House for Party

10+ 5 2


$750.00 per night

Lakefront Cottage in the woods

25+ 18 9


$950.00 per night

Guest Cottage Deckview + Pool

40+ 15 12


$2,950.00 per night

Tropical Oasis- 6 Private Rooms

20+ 12 8


$1,550.00 per night

Travel Memories

Recent Reviews

5BR Big Boulder Lake Vacation Home With Mountain Views (10)

We had a wonderful time staying in this beautiful villa in Kissimmee. The location was perfect – close to Disney World and all the other theme parks, but also quiet and peaceful. The villa itself was spacious and well-equipped, with everything we needed for a comfortable stay. We would definitely stay here again!

Elliot Price 4.83
January 18, 2022

5BR Lakefront Home Rental in Lake Harmony Poconos (34S)

“Our family of four had a fantastic time staying in this cozy cottage in Kissimmee. The proximity to Disney World was a huge plus – we could easily walk or take a short drive to the parks. The cottage was charming and well-maintained, and we appreciated the personal touches like fresh flowers and welcome gifts. We highly recommend this vacation rental!

Kian Anderson  5.00
September 1, 2021

4BR Lake House for Rent with Kayak & Dock in Poconos (36s)

“As college students, we were looking for a budget-friendly option for our trip to Florida, and this condo in Kissimmee fit the bill perfectly. It was clean and comfortable, and the location was great – just a short drive from Disney World and other attractions. We had a great time and would definitely stay here again!”

  Sam Burns  5.00
   August 26, 2021

Farmhouse Rentals with Barn for Wedding Getaways – Poconos (1735)

“We were so impressed with this luxury home in Kissimmee! It was even better than the pictures – spacious, beautifully decorated, and with all the amenities you could want. The location was perfect for our family – close to Disney World and other attractions, but also in a quiet, residential neighborhood. We would definitely stay here again and recommend it to others.”

Abigail Roberts 5.00
October 26, 2021

Mesmerising Villa/Castle for Rent with Indoor Pool in Poconos, PA (252)

“We came to Kissimmee from the west coast for our family vacation, and we were blown away by this beautiful vacation home. The location was perfect – just a short drive from Disney World and other theme parks. The home itself was spacious and well-appointed, with all the comforts of home. We had a fantastic time and would definitely stay here again.”

Lucy Hall 5.00
January 4, 2022

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!”

Lauren Harvey 5.00
February 1, 2022

Discover Other Properties

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.

Cabins for Rent

Find the perfect getaway for couples in Kissimmee.

Rentals on Lake

Find rentals on lake houses and lakefront rentals for every vacation.

Party House Rentals

Find the perfect party venue in Kissimmee for an unforgettable night.

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.

Kissimmee Map

Kissimmee is neighbour to Campbell, and Hunter’s peak, that are unincorporated territories in the state of Florida. It enjoys the company and borders of towns, stores, and local hubs like Trellis 925, tree hub, and many more.
Explore your daily life with a sense of adventure and exploration in Kissimmee. Home to the best of eye-grabbing sights and relaxing tides of nature, take your vacation for a whole lot of exploring all around the seasons. The place invites you to seek the adventure to catch the thrills that set you on cloud nine. Here’s the perfect start for a holiday you want to spend.

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.

Get in Touch

HolidayKeepers Holdings LLC.
PO Box 850 Blakeslee PA 18610

+1 609 608 6262

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