Vacation Home Rentals: Ultimate FAQ

Explore the endless possibilities for extraordinary vacation homes in Kissimmee: the Vacation Home Capital of the World, each with a unique twist tailored to exceed your getaway needs.

A beautiful vacation home rental in Kissimmee

A Kissimmee Vacation Home is your home away from home

Explore the endless possibilities for extraordinary vacation homes in Kissimmee: the Vacation Home Capital of the World, each with a unique twist tailored to exceed your getaway needs. Look through Kissimmee’s list of vacation home management properties. When you’re ready to book, visit their website.

You’ll soon realize how vast the options are and can find the perfect spot for your romantic getaway, family vacation, group trip, or family reunion. These vacation homes offer 2- to 13-bedrooms all with amenities to make your stay a memorable one – for all the right reasons. 

Your dream house is just a few clicks away.


Searching for a weekend house rental or vacation home rentals near Walt Disney World Resort, SeaWorld Orlando, Universal Studios Florida, and more in the Central Florida area? It can be overwhelming! 

Here's an ultimate frequently asked questions guide to help you find the perfect vacation home for your next trip to Kissimmee, Florida. 

A vacation home refers to a residential property that is available for short-term rental for travelers. These homes are designed to provide a comfortable and convenient accommodation option for visitors who want more space, privacy, and amenities than a traditional hotel room.

Kissimmee vacation homes can take various forms, including:

  • Single-family homes: Detached houses with multiple bedrooms, bathrooms, a kitchen, and common living areas.
  • Villas: Luxury homes with upscale features such as private pools, spacious living areas, lavishly themed rooms, private movie theater rooms, game rooms, and high-end furnishings.
  • Resort-style Homes: Homes part of larger resort communities, providing guests with access to communal facilities like pools, spas, fitness centers, restaurants, and even water parks.

Kissimmee has a wide range of vacation homes from single-family homes, luxury villas, and resort-style homes.

Some of the key features may include:

  • Fully equipped kitchens
  • Laundry facilities
  • Private pools
  • Game rooms
  • Themed bedrooms
  • Golf putting area
  • Fitness centers
  • Lazy rivers
  • Movie theater rooms

Many of these homes are located in residential neighborhoods or gated communities, offering a sense of home away from home.

Some neighborhood communities offer:

  • Arcades
  • Bike rentals
  • Fitness centers
  • Golf courses
  • Kids’ playground
  • Laundry services
  • On-site restaurants
  • Seasonal activities for the whole family
  • Shuttle service to nearby theme parks
  • Spas
  • Splash pads
  • Sports courts
  • Water parks

Plus, family-friendly activities are available, such as build your own sundae, aromatherapy crafts, bingo, tie-dye making.

Note that each property has their own amenities and add-ons, so be sure to check them out when booking.

There are more than 50,000 vacation home properties in Kissimmee, Florida. With more than 100 vacation rental properties that manage these various vacation homes throughout Osceola County, you’ll surely find the perfect property for your vacation.

  1. Start by researching various vacation rental properties in Kissimmee.
    • The best way to find your perfect spot is through the property management company websites. You can also use Vrbo as a tool to scope out a wide range of available vacation homes. However, booking directly through the property management company websites will give you deals, included amenities, further information about the neighborhood, and more.
  2. Confirm the details.
    • Look for amenities, available dates, pricing, specific rules, and distance to your favorite activities and dining.
    • Understand the booking terms, including required deposit, payment schedule, and cancellation policy.
  3. Proceed to book the vacation home once you’re satisfied with the details.
  4. Complete the payment.
  5. Receive booking details.
  6. Plan your arrival!

Kissimmee, located in Osceola County, is extremely close to the world-famous theme parks in Orlando, Florida and outdoor attractions, dining, shopping, live entertainment, and relaxation throughout the area. Plus, Kissimmee is only 25 minutes to Orlando International Airport (MCO) and 90 minutes to either coast.

Here’s an idea of just how close these vacation home neighborhoods are from area attractions:

Kissimmee has vacation homes truly for any budget and style determined by a number of factors including, time of year, length of stay, property type, and amenities.

Depending on the size of your group, a vacation home might be more economical than any other accommodation option.

Airbnb is a specific platform connecting travelers with hosts who rent out their properties for short-term stays. A vacation home is an accommodation available for rent by a property management company within a community development in Osceola County.

When you rent a home via Airbnb, a host (private entity) is renting out that home. You can search for homes by renting one room of the house, a portion of the house, or the entire home. You may be responsible for additional cleaning fees, extended stay charges, and upkeep. There are also additional rules and guidelines, as well as group size limitations when booking.

When booking a vacation home with a property management company, you rent out the entire home and have access to all the amenities on property. Plus, some properties offer additional concierge services such as private chefs, area transportation, extra housekeeping, and more.

There are more than 100 rental properties to choose from in Osceola County. These property management companies manage a variety of vacation homes in various neighborhoods throughout Kissimmee.

To browse these amazing homes, visit the property management website for more information and booking.

Here are just a few to get you started:


Encore Resort at Reunion

Jeeves Florida Rentals

Magic Village Views

Margaritaville Resort Orlando Cottages by Rentyl

Spectrum Resort Orlando

The Bear’s Den Resort Orlando

Westgate Vacation Villas

Vacation Home - a residential property that is available for short-term rental for travelers.

Property Management Company - a business or firm that is hired by property owners to oversee and handle various aspects of the day-to-day operations, maintenance, and rental of real estate properties.

Amenities - features or facilities that enhance the desirability and value of a property or a place.