Historic Downtown Kissimmee holiday rentals

We found 42 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Historic Downtown Kissimmee that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a fireplace. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Historic Downtown Kissimmee?
The most in-demand types of holiday rentals in Historic Downtown Kissimmee are houses. Prefer something different? Vrbo has numerous options to match our guests' unique requirements, so you'll see holiday homes in all shapes and sizes, and for all budgets. The perfect home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a holiday rental in Historic Downtown Kissimmee?
Several factors can influence what you'll pay for your holiday rental in Historic Downtown Kissimmee, including the season, type of property and length of stay. Still, all of our holiday homes have something in common — unbeatable value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Historic Downtown Kissimmee?
Prices for beach houses in Historic Downtown Kissimmee can vary depending on the size and style of the property and time of year you're travelling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to narrow your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Historic Downtown Kissimmee?
With 34 holiday rentals that host pets, your happy hound can join in the fun on your Historic Downtown Kissimmee holiday. Use our filter tool to browse our pet-friendly holiday rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Historic Downtown Kissimmee?
Dig out your swimsuit and inflatable lounger, because there are 32 houses with a private pool in Historic Downtown Kissimmee. Unwind at one of these superb holiday homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Historic Downtown Kissimmee?
When it comes to rental amenities that people are looking for in Historic Downtown Kissimmee, a water view, a barbecue grill and a swimming pool are at the top of the list. With Vrbo holiday homes, you'll have options to match your taste and style, whether you're planning to get away with your partner, family members or even pets.
Are there large group holiday rentals in Historic Downtown Kissimmee?
Historic Downtown Kissimmee has 22 holiday homes that can host 10 or more guests. These stays come with all the space you need to enjoy good times with your favourite people.
Are there holiday rentals in Historic Downtown Kissimmee that welcome kids?
Historic Downtown Kissimmee has 33 family-friendly holiday homes to choose from. And finding a stay that welcomes little ones is super easy with our "Properties good for families" filter. In addition to having the whole place to yourselves, you'll also get perks and amenities such as extra bedrooms, pools and kitchens.
What are the top attractions for families in Historic Downtown Kissimmee?
There are lots of cool things to do and see with the family in Historic Downtown Kissimmee, such as:

  • Fun Spot America
  • Kissimmee Go-Karts
  • Green Meadows Petting Farm

Are there holiday rentals with WiFi in Historic Downtown Kissimmee?
Historic Downtown Kissimmee has 10 holiday rentals with WiFi, so you'll be able to stay connected during your trip. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to catching up on social media, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Historic Downtown Kissimmee?
Historic Downtown Kissimmee has 31 holiday rentals where you'll be able to wind down in air-conditioned comfort. To locate a stay on Vrbo featuring this perk, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Historic Downtown Kissimmee?
The minimum required age is generally 16, 18 or 21. It can vary across properties on Vrbo, so look at the rules of your preferred Historic Downtown Kissimmee holiday home before making a booking.
How long can I rent a holiday rental in Historic Downtown Kissimmee for?
It all depends on the Historic Downtown Kissimmee property. To browse available options offering extended stays, simply type your travel dates and guest number into the Vrbo search page. Look forward to having the entire property to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and outdoor spaces where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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