Kissimmee holiday lettings

We found 31,873 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Kissimmee by choosing from 15175 houses, 1813 apartments and other holiday rentals. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Kissimmee

Showing deals for:14 Nov - 21 Nov

Image gallery for 14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

Private pool
9.8 out of 10 rating
Exceptional
(27 reviews)

14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

Kissimmee, FL

7% off
Price is £5,998
£857 nightly
Includes taxes & fees
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

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Find out more about Kissimmee

Find out more about Kissimmee

Why visit Kissimmee

  • Theme Parks Galore: Kissimmee is renowned for its proximity to world-famous theme parks, offering endless family-friendly excitement.
  • Outdoor Adventures: Enjoy a range of outdoor activities, from airboat rides in the swamps to relaxing days by beautiful beaches.
  • Charming Neighbourhoods: Explore friendly local communities filled with quaint shops and delightful dining options.
  • Diverse Accommodation: Choose from an array of holiday rentals, including spacious villas and cosy condos tailored to your needs.
  • Vibrant Cultural Scene: Experience local arts and entertainment, with various events and performances showcasing regional talent.

Popular types of accommodation in Kissimmee

Planning a getaway to Kissimmee? The next exciting step is selecting your perfect accommodation. From charming private holiday homes and spacious villas to modern condos, there’s a wide array of options to suit every traveller's needs. Whether you're seeking short-term house rentals or monthly lettings, Kissimmee has something for everyone. Discover the ideal holiday rental that offers both comfort and convenience for an unforgettable stay.

  • Houses: The top choice for visitors, offering spacious and comfortable settings for families or groups seeking a home-like experience.
  • Villas: A popular option featuring luxurious amenities, ideal for those desiring a more upscale stay in tranquil surroundings.
  • Condos: A convenient choice combining comfort and facilities, perfect for couples or small families wanting easy access to local attractions.
  • Apartments: A practical choice for those looking for self-catering options in vibrant neighbourhoods.
  • Cottages: Charming and quaint, these are perfect for a cosy retreat in a picturesque setting.**

Top attractions in and around Kissimmee

Kissimmee is an ideal destination for family holidays, entertainment, and business trips. Visitors can enjoy a variety of attractions, including theme parks, amusement parks, and arts centres. The local points of interest cater to travellers seeking family-friendly activities, outdoor adventures, and cultural experiences, ensuring there's something for everyone to enjoy during their stay in this vibrant Florida locale.

  • SeaWorld® Orlando: A thrilling theme park located 5.6km from Kissimmee, SeaWorld® Orlando offers an immersive experience with spectacular marine life shows, exciting rides, and interactive exhibits. Perfect for families, you can enjoy a day filled with adventure and education about ocean conservation.
  • Orange County Convention Center: Situated 6.2km away, this vibrant arts centre showcases a rich cultural atmosphere, hosting various events and exhibitions. It’s a fantastic place to explore the local art scene and attend engaging performances.
  • Kissimmee Lakefront Park: Located within Kissimmee, this scenic urban park boasts beautiful views of the lake, picnic areas, and walking trails, making it ideal for family outings and enjoying the outdoors in a peaceful city setting.

Things to do recommended for couples

For a romantic getaway in Kissimmee, try your hand at mini-golf at Congo River Golf, enjoy a delightful meal at Pirate's Dinner Adventure, or experience the thrill of indoor skydiving at iFly Orlando. Each spot offers a unique blend of fun and romance for couples.

Things to do recommended for families

For a memorable family holiday in Kissimmee, visit Aquatica waterpark for thrilling water rides, enjoy sports at Austin-Tindall Regional Park, or experience the excitement of karting at Kissimmee Go-Karts. Each activity promises fun and adventure for all ages!

Things to do recommended for groups

Groups visiting Kissimmee can enjoy a day at Disney Springs™ for shopping and dining, explore Old Town for entertainment and unique shops, or challenge each other at Mystic Dunes Golf Club for a round of golf in a beautiful outdoor setting.

What do I need to keep in mind when booking a vacation in 'Kissimmee

If you're travelling with a group, family, pets, or seeking longer stays, it's essential to filter according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can refine your search on Vrbo to include all of these options and more.
  • Traveling to Kissimmee with young kids: Traveling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kissimmee: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to consider including amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Kissimmee

Kissimmee, Florida, offers a delightful blend of family-friendly attractions and sunny outdoor experiences. Ideal for a family vacation, visitors can explore nearby regions boasting beautiful beach access and charming neighbourhoods filled with friendly faces. With its vibrant atmosphere, Kissimmee is perfect for those seeking both leisure and adventure, ensuring an unforgettable holiday for everyone. Whether you fancy outdoor seating or excursions, this charming city caters to all your holiday needs.

  • Four Corners: Nestled in the vibrant area of Kissimmee, Four Corners is a charming village that attracts families and outdoor enthusiasts alike. Its proximity to renowned theme parks and film studios makes it a prime location for entertainment-themed activities. Visitors can enjoy the lush landscapes of nearby golf courses and resorts, ensuring a well-rounded travel experience. With easy access to stadiums and other local landmarks, Four Corners serves as an ideal base for exploring the excitement that Central Florida has to offer.
  • Windsor Hills: Located in the heart of Kissimmee, Windsor Hills is a delightful neighbourhood that caters to families seeking fun and adventure. This area boasts a variety of shopping options and top-notch golf facilities, perfect for a leisurely day out. The close proximity to world-famous theme parks and entertainment venues enhances the travel experience, allowing visitors to easily immerse themselves in the local attractions. Windsor Hills is not only about entertainment; it also offers beautiful outdoor spaces, making it a great spot for relaxation and recreation.
  • Reunion: Reunion is a picturesque neighbourhood situated near Kissimmee, known for its outdoor activities and family-friendly atmosphere. With its stunning golf courses and luxurious resorts, it's an excellent destination for sports enthusiasts. The area is also convenient for those looking to visit nearby theme parks and film studios, ensuring a memorable holiday. Additionally, Reunion's closeness to beautiful beaches adds a unique twist to the typical Florida experience, making it a must-visit for anyone looking to explore the diverse attractions of the region.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking an extended stay often results in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new journeys, resume your previous arrangements, or organise your travel plans. You’ll see your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The sunny setting of Kissimmee is ready to explore

Take a holiday to Kissimmee and enjoy the area's festivals, entertainment and opera. Renowned for its theme park, shopping and sporting events, this city welcomes all visitors. Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are just a couple of the must-see attractions. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Kissimmee

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kissimmee a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)
  • Walt Disney World® Resort (13.6 mi / 21.9 km)
  • Magic Kingdom® Park (13.7 mi / 22 km)

Exploring the natural landscape of Kissimmee

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Kissimmee is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Lake Butler (14.4 mi / 23.2 km)

Seasonal weather in Kissimmee

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 27°C.

How to get to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.8 mi (2.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Orlando International Airport (MCO), which is 11.4 mi (18.3 km) away.

If you prefer train travel, you can make your way to Kissimmee Station. Utilise the area's public transport and catch a ride on the metro at Tupperware Station or Poinciana Station and easily see more of the city.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a holiday rental?
When considering a holiday rental in Kissimmee, Florida, a popular area to stay is the neighbourhood of Celebration. This picturesque community, originally developed by The Walt Disney Company, exudes charm with its delightful architecture and beautifully landscaped streets. It offers a tranquil atmosphere while being conveniently located near major attractions. Just a short drive away, you'll find the iconic Walt Disney World Resort, great for family outings, as well as the vibrant Disney Springs, known for its shopping, dining, and entertainment options.

Another excellent choice is the area around Lake Tohopekaliga. This region not only boasts a variety of holiday rentals but also provides stunning views and opportunities for outdoor activities such as fishing and boating. The nearby Kissimmee Lakefront Park is a wonderful spot for leisurely walks, picnics, and enjoying the local wildlife. In terms of availability, both Celebration and the Lake Tohopekaliga area offer a diverse selection of properties, suiting various preferences, from cosy villas to larger family homes.
How much does it cost to rent a holiday home in Kissimmee?
Prices for holiday rentals in Kissimmee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kissimmee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Kissimmee holiday house rentals?
You can find great discounts on house rentals in Kissimmee on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Kissimmee?
For renting a beach house in Kissimmee, Florida, travellers should consider properties near the picturesque Shingle Creek Regional Park, which offers serene natural surroundings and access to various outdoor activities. While Kissimmee is not directly on the coast, it provides proximity to several lakes, such as Lake Tohopekaliga, where visitors can find charming waterfront homes with private docks and stunning lake views. These properties often come equipped with amenities like outdoor grills, spacious decks, and private pools, superb for family gatherings or leisurely retreats. Find your rental near the beach in Kissimmee.
Are there any houseboat rentals in Kissimmee?
In Kissimmee, there are indeed houseboat rentals available, providing a unique accommodation experience on the water. These houseboats can typically be found near the picturesque lakes and waterways that the region is known for, allowing guests to enjoy beautiful views and a serene atmosphere. Amenities often include comfortable sleeping areas, fully equipped kitchens, and outdoor decks superb for relaxation and entertaining. Travellers can expect a blend of comfort and adventure as they explore nearby attractions like Walt Disney World and the vibrant local dining scene.
What is the most popular type of holiday rental accomodation in Kissimmee?
In Kissimmee, holiday houses are the most popular type of accommodation, with approximately 12,288 available throughout the area. These spacious rentals are often situated in family-friendly neighbourhoods and offer amenities such as multiple bedrooms, fully equipped kitchens, private pools, and outdoor seating areas—ideal for families or groups looking to enjoy the sunshine and relax after a day at nearby attractions like Walt Disney World and Universal Orlando. Additionally, there are around 3,384 villas that provide a similar experience but often come with more luxurious features, such as game rooms and enhanced outdoor spaces. For those seeking smaller options, about 2,030 condos and 1,323 apartments are available, typically featuring communal amenities like pools and fitness centres, along with convenient access to local shops and dining.
Are there any family house rentals in Kissimmee?
In Kissimmee, Florida, there are a substantial number of family-friendly house rentals available, with around 14,642 options for visitors to consider. This area is particularly well-known for its proximity to major attractions such as Walt Disney World and Universal Studios, making it an ideal choice for families looking to enjoy a fun-filled holiday.

Properties in Kissimmee come in a variety of sizes, ensuring there's something suitable for every group. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and private pools for relaxing after a day at the parks. Some accommodations also include game rooms, which are superb for keeping the younger ones entertained during downtime. See all family-friendly rentals in Kissimmee.
Can I rent a holiday home with a pool or hot tub in Kissimmee?
In Kissimmee, there are a staggering number of holiday homes available for rent that boast pools and hot tubs, with approximately 17,774 options to choose from. This popular destination, known for its proximity to Walt Disney World and other attractions, features various neighbourhoods where these properties can be found, including the family-friendly areas of Emerald Island and Windsor Hills, which are particularly favoured by visitors looking for a fun-filled holiday experience. Find your rental in Kissimmee with a pool or a hot tub.
Can I find long-stay holiday rentals in Kissimmee?
A long-stay holiday rental in Kissimmee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Kissimmee?
In Kissimmee, there are numerous pet-friendly house rentals available, with options exceeding three thousand. Many of these properties are conveniently located near popular attractions like Walt Disney World, making them an excellent choice for families travelling with pets. Expect amenities such as private pools, fully equipped kitchens, and spacious living areas, which cater well to both humans and their furry companions. See all pet-friendly rentals in Kissimmee.
Are there any remote work holiday rentals in Kissimmee?
In Kissimmee, Florida, there is an abundance of remote work holiday rentals, with around 18,012 options available. This vibrant destination is ideal for those looking to blend work and leisure, offering a variety of properties equipped with essential amenities for an efficient workspace. Travellers can expect features such as high-speed Wi-Fi, dedicated desk areas, laptops workspace, and sometimes even office-like setups with computer monitors and safe storage for equipment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kissimmee holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Kissimmee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Kissimmee?
In Kissimmee, popular rental amenities include a variety of options to enhance the holiday experience. Many properties feature fully equipped kitchens, which allow guests to prepare their own meals, adding convenience and flexibility during their stay. A significant number of rentals also offer access to pools, with both shared and private options available, including heated pools for year-round enjoyment.
When is the best time to visit Kissimmee for a holiday rental?
The best time to visit Kissimmee for a holiday rental is during the vibrant summer months, particularly in July. This period marks the peak tourist season, where families and adventure seekers flock to the area to make the most of its attractions, including the world-famous theme parks and outdoor activities. With temperatures averaging around 32°C, visitors can enjoy a number of experiences ranging from thrilling rides to serene boat trips on the nearby lakes.

If you're looking to enjoy the excitement of summer while avoiding the peak crowds, consider visiting in October. This month often sees a dip in prices and offers a more relaxed atmosphere, making it ideal for exploring the natural beauty of the region. The weather remains warm, with averages around 27°C, great for outdoor adventures like hiking in the nearby parks or enjoying a leisurely day at a water park.
How early should I book a Kissimmee holiday rental?
Book your Kissimmee holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kissimmee?
In Kissimmee, visitors can enjoy a variety of attractions that cater to all ages. The area is renowned for its proximity to the Walt Disney World Resort, where holiday rentals in areas like Celebration and the surrounding neighbourhoods provide easy access to the parks. Celebration, originally designed by Disney, offers charming streets, restaurants, and beautiful architecture, making it a delightful place to stay.

For those interested in outdoor activities, Kissimmee's Lake Tohopekaliga is a great spot for fishing, boating, and birdwatching, with several holiday homes nearby that offer waterfront views. The area also boasts the scenic Shingle Creek Regional Park, which features nature trails and picnic areas, ideal for families and nature enthusiasts.
Can I change or cancel my Kissimmee home rental booking on Vrbo?
To find Kissimmee holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Kissimmee holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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