Top Kissimmee houses - Orlando

Explore Kissimmee house rentals

The Ultimate 10,350 sq ft Orlando Estate - Your Private Resort Near Disney

Sleeps 28 · 8 bedrooms · 9+ bathrooms

Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

Sleeps 38 · 14 bedrooms · 14+ bathrooms

Top rated house rentals - Kissimmee

Waterside was perfect!

Waterside is a great villa, great location for Disney and Universal parks. Also a great location for grocery shopping and places for eating out.The villa it’s self is great, very clean and wellMaintained had everything that we needed while there. Kids enjoyed the pool and games room. Will definitely be our first choice of villa when coming back to Orlando and have already advised friends and family about it. 10/10 experience

James H.

Stayed Jun 2025

Enjoy a swim with your family in your private heated pool or unwind in the spa.

Premier Host

Lovely House in Great Location

Stayed at this property with wife and daughter whilst in the Kissimmee area and found it to be exactly what we wanted. It was extremely clean and spacious and could comfortably sleep 8 people. The neighbourhood is nice and quiet which is exactly what we were looking for. Highly recommended

Ian L.

Stayed Aug 2024

Communal Water Park with Heated Jacuzzis and Waterfall Features.

Premier Host

Wonderful stay in Orlando

This is a really lovely house. We were a group of five adults and two children and it was perfect for us. It was all very comfortable, clean and well equipped - perfectly located for Disney but in a quiet residential area. Our hosts could not have been more helpful and responsive. We had a problem with our flight at the end of the stay because it was delayed until the next morning, but Otto helped us to arrange another nights stay at the house within a couple of hours which was so appreciated. The check in and check out process was extremely easy and made for a really relaxed stay. Thank you so much for a brilliant holiday! We wouldn't hesitate to recommend this property or to stay again.

Caroline M.

Stayed Jul 2024

Premier Host

Craig

Property was in a perfect location for both Disney and Universal parks, just a short drive away. Really easy access and communication with the owner was great. We couldnt have asked for a better place to stay

Craig J.

Stayed Apr 2024

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Frequently asked questions

Are there any holiday home rentals in Kissimmee?

Choose one of our 24,753 holiday home rentals in Kissimmee and you'll have the perfect base for your next great adventure. Historic Downtown Kissimmee, Mill Run and Magic Landings are some of the city's most sought-after areas.

How much does it cost to stay in a holiday rental house in Kissimmee?

Whether you're seeking an affordable getaway or a luxurious retreat, we offer a variety of holiday home rentals in Kissimmee to choose from. Use our filters to compare prices and find the best place for you and your crew.

When is the best time to rent a holiday house in Kissimmee?

The ideal time is whenever you can slip away from your everyday routine and enjoy the weather you like most. For many Vrbo guests searching for a holiday home rental in Kissimmee, Orlando, that's March. Average temperatures during this month range from 15ºC (59ºF) to 25ºC (77ºF).

Where can I rent a Kissimmee holiday house with great views?

Whether it's the sea, a river or the bright lights of the city, a holiday home rental is always better with a view. No matter where you want to base yourself in Kissimmee, we'll help you find a house with picture-perfect outlooks. Simply click on the "Popular" button at the top of the page, then select the filters that'll refine your search.

Does Kissimmee have any weekend house rentals?

You'll discover some terrific houses that are available for weekend rental. Simply key in your travel dates and get ready for a fun-packed few days away. If you can't find the perfect holiday home rental in Kissimmee straight away, just alter your dates and search again.

Are there any pet-friendly house rentals in Kissimmee?

With 220 pet-friendly holiday home rentals in Kissimmee, you can enjoy your next big trip with your furry friend by your side. On top of comfy beds for everyone, lots of houses also come with features like doggie bowls and free treats. See what's available by selecting the "Pets allowed" filter.

What are the top things to do in Kissimmee?

Get your Kissimmee getaway off to a terrific start by visiting top-rated sights like Disney's Animal Kingdom® Theme Park, Orange County Convention Centre and Epcot®. Stay in a Vrbo holiday home rental with the family and then explore this destination's wonders together.

Why should I book my holiday rental house with Vrbo?

Excellent customer support from the moment you book until after your trip is among several reasons to choose us for your holiday home rental. We also offer properties that go beyond the traditional hotel room — think houses in spectacular locations, whether that's by the beach or high in the mountains. Plus, with our One Key™ rewards programme, you'll be able to collect and use OneKeyCash™* on eligible bookings with Vrbo. And with flexible cancellation policies and benefits like cancellation protection, we offer peace of mind. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.