Kissimmee Vacation Rentals

Kissimmee Vacation Rentals By Owner

Start searching for family friendly Kissimmee rentals near major theme parks like Disney, Universal, and Legoland. Find resort homes, condos, house rentals with private pools and more below.

Neighborhoods in Kissimmee Vacation Rentals

Modern 10 Bedroom Home - Only Minutes from Disney!

Kissimmee Vacation Rentals
10/BR 8/BA SLEEPS 16

Dreams Come True - Kissimmee Vacation Rental with Private Pool and Hot Tub - Emerald Island Resort Near Disney - Sleeps 14

Kissimmee Vacation Rentals
7/BR 5/BA SLEEPS 14

Brand New Private Pool Villa in Storey Lake Resort

Kissimmee Vacation Rentals
5/BR 5/BA SLEEPS 12

Close to Disney and golf! Paradise Palms resort for relaxing nights after adventurous days, 4bd/3ba with private pool

Kissimmee Vacation Rentals
4/BR 3/BA SLEEPS 10

South facing heated pool and spa

Kissimmee Vacation Rentals
6/BR 4/BA SLEEPS 12

LUXURY UPGRADED POOL HOME IN PRIVATE GATED COMMUNITY

Kissimmee Vacation Rentals
4/BR 3/BA SLEEPS 8

Windsor Hills Resort Private Pool Home

Kissimmee Vacation Rentals
6/BR 4/BA SLEEPS 14

Florida Sunsations Kissimmee Condo Rental from $99 nt - Near Disney

Kissimmee Vacation Rentals
3/BR 2/BA SLEEPS 8

Amazing Luxury Pool Villa @ Storey Lake mins from Disney

Kissimmee Vacation Rentals
9/BR 5/BA SLEEPS 20

Stylish south facing Villa with private pool

Kissimmee Vacation Rentals
4/BR 3/BA SLEEPS 8

Tropical Paradise Villa Your Perfect Disney Trip Begins Here - Kissimmee Vacation Rental with Private Pool

Kissimmee Vacation Rentals
4/BR 2/BA SLEEPS 8

8913 Rhodes

Kissimmee Vacation Rentals
6/BR 4.5/BA SLEEPS 12

Luxury villa with private south-facing pool and private home theater

Kissimmee Vacation Rentals
7/BR 5.5/BA SLEEPS 16

101 Happy Memories Florida Villa - Pool, Game Room, Mins from Disney

Kissimmee Vacation Rentals
7/BR 6/BA SLEEPS 14

SUNSHINE ESCAPE VILLA -Saltwater South Pool

Kissimmee Vacation Rentals
6/BR 4.5/BA SLEEPS 16

Mickey décor (April 21-29) (3 bed / 3 bath Townhouse w/ heated Pool

Kissimmee Vacation Rentals
3/BR 3/BA SLEEPS 8

6 Bed 5.5 Bath Disney Dream Home In The Emerald Island Resort - Sleeps 12

Kissimmee Vacation Rentals
6/BR 5/BA SLEEPS 12

551-Luxury Villa Private Pool-Hot Tub-Game Room

Kissimmee Vacation Rentals
8/BR 7/BA SLEEPS 18

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Kissimmee Vacation Rentals 

Kissimmee, Florida is a popular destination for travelers seeking sunshine and adventure. Located just south of Orlando, Kissimmee is home to a wide range of attractions, including theme parks, nature preserves, and cultural landmarks. Many visitors come to explore the famous theme parks, such as Walt Disney World, Universal Studios, and SeaWorld. In addition to theme parks, Kissimmee boasts several outdoor recreation options, including airboat rides through the Everglades, hiking and biking trails, and fishing in local lakes. Travelers can also experience the region's rich history and culture at sites like the Osceola County Historical Society Museum, the Zora Neale Hurston National Museum of Fine Arts, and the Silver Spurs Rodeo. No matter what your interests, Kissimmee offers a diverse range of activities and attractions to keep visitors entertained.

  • Hosts often rent homes from 1 night to weekly minimum stays with flexible check in days. 

The check-in day for vacation rentals in Kissimmee, Florida can vary depending on the individual host or property management company. However, many vacation rental hosts in Kissimmee allow check-ins every day of the week, including weekends. It is always a good idea to check with the specific vacation rental host or management company to confirm their check-in policies and procedures.

Is Kissimmee a good place to rent a Vacation Rental?

Yes, Kissimmee can be a great place to rent a vacation rental. The city is located in central Florida, close to major theme parks like Walt Disney World, Universal Studios, and SeaWorld, which makes it a popular tourist destination. Vacation rentals in Kissimmee can offer visitors more space, privacy, and amenities than a traditional hotel room, making it a great choice for families or groups traveling together. Additionally, many vacation rental properties in Kissimmee feature amenities like private swimming pools, game rooms, and outdoor grills, adding to the overall vacation experience. It's important to do your research, read reviews, and work with reputable vacation rental companies or hosts to ensure a smooth and enjoyable vacation rental experience.

What do I need to know to rent a vacation home in Kissimmee?

  1. Research vacation rental properties on FLARBO: Look for reputable vacation rental companies or hosts with good reviews and ratings. Read through the property descriptions and amenities to ensure the rental meets your needs and preferences.
  2. Understand the rental agreement: Make sure to read and understand the rental agreement and any policies or restrictions, such as check-in/check-out times, pet policies, and occupancy limits. Ask any questions you may have before booking to avoid any confusion or surprises during your stay.
  3. Check the location: Kissimmee is a large area with various neighborhoods and developments, so make sure to check the location of the vacation rental in relation to the activities and attractions you want to visit. Consider factors such as proximity to theme parks, restaurants, and shopping centers.
  4. Confirm the amenities: Confirm the amenities included with the rental, such as kitchen appliances, linens, towels, and any recreational activities or equipment. Some rentals may offer additional amenities such as a private pool or hot tub, game room, or grill.
  5. Plan for transportation: If you're planning to visit attractions outside of the rental area, consider renting a car or arranging for transportation in advance. Some rentals may offer information on shuttle services to nearby theme parks or attractions.
  6. Understand payment and cancellation policies: Make sure you understand the host's payment and cancellation policies for the rental, including any security deposits or fees. Some rentals may require payment in advance, while others may offer a flexible cancellation policy.
  7. Communicate with the rental company or host: Communication is key when renting a vacation home. Make sure to ask any questions you may have before and during your stay, and notify the rental company or host of any issues or concerns as soon as possible.
Typical Stay Periods

Kissimmee vacation rentals can be rented as follows depending on the host's preference.

  • nightly
  • weekly
  • monthly
Typical Turnover Day

Kissimmee vacation rentals may have a Friday or Saturday turnover date during high season. More flexible check-in and out dates are found during low and shoulder seasons. Although the turnover date can vary by host.

Any Day of the Week - Depending on the Host

Kissimmee Vacation Rental Price Information
  • Low range from $90 per night - $630 per week - $2,700 per month
  • High range from $668 per night - $4,676 per week - $20,000 per month
Booking Window

It's recommended to book a vacation rental in Kissimmee, Florida as early as possible, especially during peak travel seasons or when attending major events such as holidays or festivals. The booking window for vacation rentals can vary depending on factors such as the time of year, the popularity of the rental, and the number of vacation rentals available.

In general, the earlier you book a vacation rental in Kissimmee, the better chance you have of securing your preferred rental and dates. It's not uncommon for travelers to book vacation rentals up to a year in advance, particularly for popular vacation spots and high season dates.

That being said, if you're flexible with your travel dates and accommodations, you may be able to find last-minute deals or discounts on vacation rentals in Kissimmee. It's always a good idea to check with vacation rental companies or hosts for any specials or promotions that may be available.

Guest Retention

Kissimmee, Florida is a popular tourist destination, with many visitors returning year after year. The guest retention in Kissimmee can vary depending on factors such as the quality of the vacation rental experience, the activities and attractions available, and the overall appeal of the destination.

Many vacation rental hosts and companies in Kissimmee have repeat guests who return year after year, which is a good indication of high guest retention. This is likely due to the variety of activities and attractions available in the area, including theme parks, outdoor recreation, and cultural landmarks.

Additionally, Kissimmee's central location in Florida makes it a convenient destination for travelers visiting other parts of the state. Some visitors may stay in Kissimmee as a base for exploring other nearby areas or attractions, which can also contribute to guest retention.

Overall, Kissimmee has a strong reputation as a top tourist destination, and many visitors return to the area for its attractions, amenities, and overall vacation experience.

High Season
Kissimmee High Season - January to April and June to August

The high season for visiting Kissimmee, Florida typically runs from January through April, with peak season being in March. This is due to several factors, including the mild weather, popular events and festivals, and school holidays.

During this time, the area sees an influx of tourists, particularly families with children on spring break. Accommodations, including vacation rentals, can be in high demand and may be more expensive than during other times of the year.

Additionally, the summer months from June through August can also be considered high season due to the warmer weather and summer break for schools. This time of year may be more crowded at theme parks and other attractions.

Low Season
Kissimmee Low Season - May, September to December

It's important to keep in mind that high season can vary depending on the specific events and attractions in the area, so it's always a good idea to check the calendar of events and plan accordingly. If you're looking to avoid the crowds and potentially save on accommodations, consider visiting Kissimmee during the off-season months, such as May or September through December.

Kissimmee Family Friendly Rentals

Kissimmee is home to a variety of activities and attractions that cater to all ages, making it an ideal spot for families with children of different ages and interests.

One of the most popular attractions in Kissimmee is the Walt Disney World Resort, which includes four theme parks, two water parks, and a variety of entertainment and dining options. Additionally, there are several other theme parks and attractions in the area, including Universal Orlando Resort, SeaWorld Orlando, LEGOLAND Florida, and Gatorland.

Kissimmee also offers plenty of outdoor activities and attractions for families, such as airboat tours, fishing, hiking and biking trails, and nature parks. The area is also home to several championship golf courses, which can be a fun activity for the whole family to enjoy.

In terms of accommodations, there are plenty of vacation rental options in Kissimmee, including houses, condos, and villas, that can provide families with more space and amenities than a traditional hotel room.

Overall, Kissimmee is a great destination for families looking to create unforgettable memories and experiences together.

  • 90% of the vacation rentals in the Kissimmee location are considered family-friendly
Kissimmee Rentals with Pool and Hot Tubs

During your vacation, you will spend most of your time outdoors. Kissimmee offers several options for recreational activities, including swimming pools and hot tubs, making it a great destination to visit throughout the year.

Kissimmee Rental Property Types

Kissimmee offers a wide variety of vacation rental options, with the majority consisting of condos and private homes. You will find numerous types of dwellings available to suit your needs and preferences.



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