Kissimmee vacation rentals

We found 31,567 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Kissimmee by choosing from 1556 houses, 90 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Kissimmee

Showing deals for:Jun 5 - Jun 12

Image gallery for 7 BEDS/7 BATHS,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN DISNEY

Front View
9.4 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)

7 BEDS/7 BATHS,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN DISNEY

Kissimmee

5% off
Price is CA $449
CA $4,207 total
includes taxes & fees
7 BEDS/7 BATHS,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN DISNEY

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Find out more about Kissimmee

Why visit Kissimmee

  • Proximity to Theme Parks: Kissimmee is ideally located near world-famous theme parks, offering endless family fun and adventure.
  • Beautiful Lakes: Enjoy picturesque lakes perfect for outdoor activities like fishing, boating, and relaxing by the water.
  • Unique Vacation Rentals: Experience a variety of accommodations, from charming homes to spacious villas, tailored to any group size.
  • Friendly Atmosphere: The welcoming vibe of Kissimmee enhances your vacation, making you feel right at home.
  • Cultural Experiences: Explore local attractions that provide a blend of cultural and outdoor adventures for all ages.

Popular types of accommodation in Kissimmee

If you’re looking for the perfect getaway in Kissimmee, you’re in the right place. Our vacation rental options include charming houses, spacious villas, and comfortable condo rentals. Whether you're after a friendly rental for the whole family or a cozy spot for a romantic retreat, we have a variety of choices to suit your needs. Enjoy a memorable stay with the reassurance that comes from booking with us.

  • Houses: These are the top choice for visitors in Kissimmee, offering spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Villas: A close second, villas provide a luxurious experience with upscale amenities and often feature private pools.
  • Condos: Popular among couples and small families, condos offer convenience and access to shared facilities.
  • Apartments: Ideal for budget-conscious travelers, apartments provide essential amenities in a home-like setting.
  • Cottages: A charming option, cottages provide a cozy retreat with a touch of rustic charm.**

Top attractions in and around Kissimmee

Kissimmee, Florida, is an ideal destination for family vacations, business trips, and entertainment-themed getaways. Visitors can explore popular attractions such as theme parks, amusement parks, and beautiful lakes, catering to those seeking family fun, outdoor adventures, and cultural experiences. To enhance your stay, consider adventure with Kissimmee vacation rentals for a unique and comfortable experience during your visit.

  • Universal Orlando Resort: Experience thrilling rides and attractions inspired by your favourite movies. This vibrant theme park offers a fantastic family atmosphere, ensuring fun for all ages just 20.9km from Kissimmee.
  • Orange County Convention Center: A hub for arts and culture, this convention centre hosts a variety of events and exhibitions. Immerse yourself in the local arts scene, located 16.1km away from Kissimmee.
  • Kissimmee Lakefront Park: Enjoy a beautiful urban park in the heart of Kissimmee, featuring scenic waterfront views, playgrounds, and picnic areas, perfect for family outings and outdoor activities.

Things to do recommended for couples

For a romantic getaway in Kissimmee, try your hand at mini-golf at Pirate's Island Adventure Golf, indulge in a delightful dinner at Pirate's Dinner Adventure, and unwind with a tasting at True Blue Winery. Each experience offers a unique blend of fun and romance, perfect for couples.

Things to do recommended for families

Your family vacation in Kissimmee will be filled with excitement. Enjoy a splashing day at Disney's Typhoon Lagoon Water Park, unleash your adventurous spirit at Wonderworks, and race each other at Kissimmee Go-Karts. These experiences promise fun and adventure for all ages.

Things to do recommended for groups

In Kissimmee, groups can enjoy a shopping spree at Disney Springs™, explore the lively Old Town for entertainment and dining, and hit the greens at Mystic Dunes Golf Club for a fun day outdoors. These activities offer a perfect blend of local culture and adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with friends, family, pets, or considering an extended stay, it’s important to prioritize your needs while searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily apply filters for these options, and much more, on Vrbo.
  • Traveling to Kissimmee with young kids: Traveling with young kids can be a bit of a challenge. It's important to prioritize their comfort and safety, along with amenities that suit their age, 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 vacation isn't truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like food bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're in search of vacation rentals offering discounts for extended 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Kissimmee

Kissimmee, Florida, offers an ideal family getaway with its sunny weather and proximity to famous theme parks. Explore unique attractions, enjoy water views, and bask in the friendly atmosphere of the city and surrounding areas. Whether you're seeking adventure or relaxation, Kissimmee promises a memorable vacation experience filled with excursions and charming neighborhoods, making it the perfect destination for a fun-filled escape in the Sunshine State.

  • Orlando: As a vibrant metropolis, Orlando serves as a major hub for family entertainment and outdoor adventures. Located just a short drive from Kissimmee, this city is famed for its world-class theme parks, including Walt Disney World and Universal Studios. Visitors can also explore the city's shopping areas, indulge in fine dining, or enjoy cultural experiences at local arts centres. With a variety of beaches and film studios nearby, Orlando offers a diverse range of attractions that cater to all ages, making it an essential stop on your vacation.
  • Four Corners: Nestled in the vicinity of Kissimmee, Four Corners is a charming village that appeals to families seeking both relaxation and entertainment. This area boasts numerous resorts, as well as golf courses that cater to avid golfers and leisure seekers alike. With its close proximity to popular theme parks and film studios, Four Corners serves as an ideal base for those looking to explore the thrilling attractions of Central Florida, while enjoying a quieter, family-oriented atmosphere.
  • Windsor Hills: Located just around the corner from Kissimmee, Windsor Hills is a welcoming neighbourhood perfect for families and those looking for outdoor activities. Known for its luxurious resorts and shopping areas, this community offers a laid-back environment while still being close to iconic attractions like theme parks and stadiums. Whether you're lounging by the pool or teeing off at a nearby golf course, Windsor Hills provides a delightful mix of relaxation and adventure, making it a must-visit during your stay in the area.

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. Happy planning.

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a convenient way to plan your travels, allowing you to create new trips, pick up where you last left off, or easily view and organize your itineraries. You can find all the properties you’ve saved or booked in the Potential, Upcoming, or Current Trips sections. To start using the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The sunny setting of Kissimmee is ready to explore

Take a vacation 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-sees. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Kissimmee

Do you want to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kissimmee a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 an outdoor enthusiast or just want to spend some time taking in the scenery, Kissimmee is a great place to get out in nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Cecile (4.9 mi / 8 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)

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 81°F.

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 center. If you're unable to find a flight that fits your schedule, you can also fly into Orlando Intl. Airport (MCO), which is 11.4 mi (18.3 km) away.

If you're traveling by train, the main station is Kissimmee Station. Consider catching the metro at Tupperware Station or Poinciana Station to see more of the city.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a vacation rental?
When considering a vacation 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 vacation home in Kissimmee?
Prices for vacation 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 travelling 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.
Are there any discounts for Kissimmee vacation 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 vacation 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 vacation rental accomodation in Kissimmee?
In Kissimmee, vacation houses are the most prevalent type of vacation 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 vacation 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 vacation rental market, with about 14,832 options available. Similar to vacation 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 vacation 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. See all family-friendly rentals in Kissimmee.
Can I rent a vacation home with a pool or hot tub in Kissimmee?
In Kissimmee, there are an impressive number of vacation 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 vacation rentals in Kissimmee?
A long-stay vacation 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 vacation rentals in Kissimmee?
In Kissimmee, Florida, there is a substantial selection of remote work vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rental?
The peak season for visiting Kissimmee is during the summer months of June to August, with July being the most popular time for vacation 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 vacation 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 vacation rental?
Book your Kissimmee vacation 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 vacation 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 vacation 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 vacation 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.

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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