Kissimmee holiday lettings

We found 31,367 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Kissimmee by choosing from 1561 houses, 93 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:3 Jul - 10 Jul

Image gallery for Stylish and Cozy Pool Home near Disney in a Gated Community

Newly surfaced pool facing conservation area!
9.6 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)

Stylish and Cozy Pool Home near Disney in a Gated Community

Kissimmee

8% off
Price is £3,169
for 7 nights, 1 villa
£453 per night
includes taxes & fees
Stylish and Cozy Pool Home near Disney in a Gated Community

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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 Hollywood Studios® (10.3 mi / 16.6 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)

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)
  • Little Lake Bryan (8.1 mi / 13.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 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 vicinity around the Old Town district. This charming area offers a vibrant setting with a variety of shops, restaurants, and entertainment options. Old Town is well-known for its classic car shows and amusement rides, making it a delightful spot for families and car enthusiasts alike.

Another excellent neighbourhood to explore is the area near Lake Tohopekaliga, which provides stunning views and opportunities for outdoor activities such as fishing and boating. The serene environment is complemented by parks and walking trails, superb for those looking to unwind amidst nature.

In terms of rental properties, Kissimmee boasts a considerable selection, with options ranging from cozy apartments to spacious villas, suiting various group sizes and budgets.
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, the area around Lake Tohopekaliga offers a scenic setting with access to various water activities. Many holiday rentals here come equipped with amenities such as private docks, outdoor grills, and spacious patios, superb for families or groups looking to enjoy lakefront living. Properties often feature modern kitchens and large living areas to accommodate social gatherings after a day spent enjoying the water.

Additionally, the nearby Shingle Creek Regional Park provides opportunities for hiking and nature walks, and many rentals in this area may include features like screened porches or balconies that allow guests to fully appreciate the natural surroundings. The proximity to local attractions in Kissimmee, including theme parks and dining options, enhances the appeal for travellers seeking both relaxation and entertainment. Find your rental near the beach in Kissimmee.
Are there any houseboat rentals in Kissimmee?
In Kissimmee, several houseboat rentals are available, offering a unique way to experience the area. These houseboats typically feature amenities such as comfortable living spaces, fully equipped kitchens, and outdoor decks for enjoying the scenic views of the water. Located near popular attractions like the Walt Disney World® Resort and the beautiful lakes in the vicinity, these rentals provide a tranquil escape while still being close to the excitement of theme parks and recreational activities.
What is the most popular type of holiday rental accomodation in Kissimmee?
In Kissimmee, holiday houses are the most prevalent type of holiday rental, with approximately 47,280 available throughout the area. These spacious properties are often situated in family-friendly neighbourhoods, making them ideal for those visiting nearby attractions like Walt Disney World® and Universal Studios. Most holiday houses come equipped with multiple bedrooms, fully equipped kitchens, and private pools or outdoor areas, providing ample space for relaxation and entertainment.

Villas also feature prominently in the holiday rental market, with about 14,832 options available. Similar to holiday houses, villas typically offer luxurious amenities, including private pools, game rooms, and expansive living spaces, suiting families and larger groups seeking comfort during their stay.

Condos and apartments are also available, with around 9,384 and 5,372 units respectively, often located in resort-style complexes that provide additional facilities like communal pools and fitness centres.
Are there any family house rentals in Kissimmee?
In Kissimmee, Florida, there is a remarkable selection of family-friendly holiday rentals—approximately 14,799 available throughout the area. This vibrant locale is renowned for its proximity to major attractions like Walt Disney World® and Universal Studios, making it a prime choice for families.

Properties in Kissimmee often include spacious living areas, fully equipped kitchens for preparing family meals, and private outdoor spaces where children can play. Many homes feature amenities such as private pools, game rooms, and even themed bedrooms, offering a delightful experience for younger guests.

Moreover, the surrounding neighbourhoods, including Celebration and Davenport, provide additional options for families seeking a blend of convenience and comfort. With access to local parks, restaurants, and shops, visitors will find everything they need for an enjoyable stay.
Can I rent a holiday home with a pool or hot tub in Kissimmee?
In Kissimmee, there are an impressive number of holiday homes available for rent that feature pools and hot tubs, with around 17,963 options to choose from. This popular destination in Florida is renowned for its proximity to theme parks and attractions, making it an ideal spot for families and groups seeking a fun-filled getaway.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, spacious patios for outdoor dining, and fully equipped kitchens great for self-catering. Many properties are designed with comfort in mind, often featuring multiple bedrooms, living areas, and entertainment options such as game rooms or home theatres. Additionally, some homes may offer convenient access to community facilities like clubhouses and fitness centres. 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 is a wide selection of pet-friendly house rentals available, with over 3,000 options to choose from. Many of these properties come equipped with amenities such as private pools, spacious backyards, and fully equipped kitchens, making them ideal for families or groups travelling with pets. The rentals often feature open-plan living areas, multiple bedrooms, and convenient laundry facilities, ensuring a comfortable stay.

The area is also well-situated for outdoor activities, with several parks and nature reserves nearby where pets can enjoy the fresh air. For instance, Lakefront Park offers walking trails and picnic areas, great for a day out with your furry friend. Additionally, Kissimmee has various pet-friendly dining options, allowing you to enjoy meals without leaving your pet behind. See all pet-friendly rentals in Kissimmee.
Are there any remote work holiday rentals in Kissimmee?
In Kissimmee, Florida, there is a substantial selection of remote work holiday rentals, with over 73,000 options available. This vibrant area, located near popular attractions such as Walt Disney World® and Universal Studios, is ideal for those looking to combine work and leisure. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi and dedicated workspaces, ensuring a productive environment while enjoying the comforts of home.

Travellers can expect a variety of accommodation types, from spacious villas with private pools to cosy apartments. Many rentals include features such as fully equipped kitchens, laundry facilities, and outdoor areas for relaxation. The proximity to local shops, restaurants, and recreational activities adds to the appeal, allowing guests to unwind after a day of work. 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 fully equipped kitchens, allowing guests to prepare their meals conveniently. Many properties also feature coffee and tea makers, ideal for a quick morning pick-me-up before heading out to explore the area. Onsite parking is commonly available, which is especially convenient for those travelling with their own vehicles. Additionally, both private and shared pools are prevalent, providing refreshing options for relaxation after a day at the nearby theme parks or outdoor attractions.
When is the best time to visit Kissimmee for a holiday rental?
The peak season for visiting Kissimmee is during the summer months of June to August, with July being the most popular time for holiday rentals. This vibrant period attracts families and adventure seekers eager to enjoy the nearby theme parks, water attractions, and outdoor activities. With temperatures typically soaring between 25 to 33 degrees Celsius, visitors can take full advantage of the sunny skies while exploring the various attractions that Kissimmee has to offer.

During these summer months, the atmosphere is lively, with plenty of events and activities designed for all ages. Families can take part in the excitement of attractions like Walt Disney World® and Universal Studios, or cool off at water parks, ensuring a memorable holiday experience.

For those looking for a more budget-friendly option, consider visiting in October. This month provides a wonderful opportunity to enjoy the pleasant climate, with temperatures ranging from 20 to 28 degrees Celsius, while avoiding the crowds. October also brings a unique charm to Kissimmee, as visitors can experience local autumn festivals and the beautiful fall foliage in the surrounding areas.

In summary, your choice of when to visit Kissimmee depends on whether you prefer the bustling energy of the summer peak season or the more relaxed atmosphere of the autumn months.
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 range of attractions that cater to all ages. The area is renowned for its proximity to the Walt Disney World® Resort, making it a prime spot for families looking to experience the magic of theme parks. The nearby Old Town offers a charming blend of shopping, dining, and entertainment, featuring classic car shows and amusement rides that evoke nostalgia.

For outdoor enthusiasts, Lake Tohopekaliga provides opportunities for fishing, boating, and wildlife viewing, offering a serene escape from the hustle and bustle of the theme parks. The Kissimmee Prairie Preserve State Park is another highlight, showcasing beautiful landscapes and a chance to spot unique birds and wildlife, particularly during the migratory seasons.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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