Some info has been automatically translated. Show original language
Airbnb your place

Vacation rentals in Kissimmee

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kissimmee vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Kissimmee's top sights

Kissimmee Lakefront Park138 locals recommend
Kissimmee Gateway Airport8 locals recommend
Gatorland418 locals recommend

Other great vacation rentals in Kissimmee

Top guest favorite
An inviting pool area glows in soft blue light against the evening sky. The expansive pool features a raised hot tub, surrounded by lounge chairs and palm trees. Lush greenery enhances the serene atmosphere, creating a perfect retreat for relaxation.
Home in Kissimmee
5 out of 5 average rating, 23 reviews

Blissful Pool Villa • Bears Den • 6mi to Disney

Top guest favorite
A serene outdoor area features a winding pool with an integrated spa, surrounded by poolside loungers in vibrant blue. A shaded dining area is visible, set against a backdrop of meticulously maintained greenery and a clear blue sky.
Home in Kissimmee
4.94 out of 5 average rating, 16 reviews

Gorgeous 5BR @Encore next to Disney - 7710

Top guest favorite
An aerial view of Boggy Creek Manor showcases the spacious property surrounded by greenery and mature trees. The single-story home features a welcoming entrance and a carport, while open areas invite exploration and relaxation across the expansive 5 acres.
Home in Orlando
5 out of 5 average rating, 17 reviews

Boggy Creek Manor – A Cozy Orlando Farm Retreat

Guest favorite
A vibrant game room designed with a Super Mario theme features a red pool table and an arcade-style gaming station. Colorful wall graphics and playful carpet add to the inviting atmosphere. Comfortable gaming chairs are positioned near a desk, creating a fun environment for guests.
Home in Kissimmee
5 out of 5 average rating, 8 reviews

4561 Majestic 9BD Kingdom Retreat Near Disney

Top guest favorite
A vibrant game room features a colorful mural of iconic anime characters in dynamic poses on one wall. A decorative statue stands nearby, while a wooden bench runs along the side, providing comfortable seating. The space is illuminated by soft overhead lighting and decorated with dark curtains.
Townhouse in Kissimmee
5 out of 5 average rating, 71 reviews

Full Arcade~ Resort ~Heated Pool~Anime Adventure!

Top guest favorite
The exterior of the single-family home is illuminated at night, highlighting the garage and front entrance. Soft lighting accentuates the landscaped garden and driveway, creating a welcoming entrance. The home's design features a combination of stone and stucco, framed by a well-maintained lawn.
Home in Kissimmee
4.96 out of 5 average rating, 81 reviews

“Casa Del Sol”

Top guest favorite
An outdoor area with a screened enclosure showcases a private pool surrounded by a well-maintained yard. Lounge chairs are positioned near the water, and pathway stones lead to the pool, illuminated by soft lights above. The evening sky adds a serene backdrop.
Home in Kissimmee
4.96 out of 5 average rating, 98 reviews

Kissimmee/20 min to Disney/Private Heated Pool

Guest favorite
A themed game room is displayed, featuring a large pool table and a ping pong table. The walls are decorated with space-themed murals, while colorful lighting adds a dynamic ambiance. An arcade machine is positioned in one corner, inviting guests to enjoy recreational activities.
Home in Kissimmee
5 out of 5 average rating, 12 reviews

Wonderful House Near Disney

Show all

Quick stats about vacation rentals in Kissimmee

  • Total rentals

    7.3K properties

  • Total number of reviews

    251K reviews

  • Family-friendly rentals

    6.1K properties are a good fit for families

  • Pet-friendly rentals

    1.1K properties allow pets

  • Rentals with a pool

    6.6K properties have a pool

  • Rentals with dedicated workspaces

    4K properties have a dedicated workspace

Frequently Asked Questions

  • How is the weather in Kissimmee?

    Kissimmee boasts a tropical climate, with hot, humid summers reaching 90°F (32°C) and milder winters averaging around 60°F (15°C). Rainfall is more frequent in the summer, while winter tends to be drier.

  • What are some of the best things to do in Kissimmee?

    Popular activities in Kissimmee include exploring the Old Town, a recreated Florida town full of shops and restaurants, taking a thrilling airboat tour on Lake Tohopekaliga, or enjoying a round of golf at one of the city's many golf courses.

  • What is the best time of year to visit Kissimmee?

    The most popular time to visit Kissimmee is in the summer, particularly between March and August. During this period, the city hosts local events such as the Kissimmee Sunshine Regional Chili Cook-Off and the Silver Spurs Rodeo.

  • What are the best places to stay in Kissimmee?

    Celebrate, a family-friendly community, is often recommended for its proximity to theme parks. Downtown Kissimmee is popular for its vibrant nightlife and historic landmarks. West Kissimmee, located close to a number of natural attractions, is also frequently suggested.

  • What are the best places to visit in Kissimmee?

    Popular places to visit in Kissimmee include the Kissimmee Lakefront Park, the Osceola County Historical Society Pioneer Village, and Gatorland, a wildlife preserve and theme park.

  • What are some hiking trails in Kissimmee?

    Kissimmee has a variety of hiking trails such as the Shingle Creek Regional Trail for scenic views of natural Florida or the Disney Wilderness Preserve which is home to numerous species of plants and animals.

  • What are some family activities to do in Kissimmee?

    Families in Kissimmee can explore numerous attractions including the interactive exhibits at the Museum of Military History, a fun-filled day at Fun Spot America amusement park, or a chance to spot native Florida wildlife at the Wildlife Refuge.

  • What are some of the best day trip ideas in Kissimmee?

    Popular day trips from Kissimmee often include a visit to Orlando, just 17 miles (27 km) away, to experience its world-renowned theme parks. Alternatively, the beautiful beaches of Clearwater are just 90 miles (145 km) away.

  • What types of vacation rentals are available in Kissimmee?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Kissimmee. From over 500 apartment rentals, over 710 villa rentals to over 3,540 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Kissimmee?

    Yes! Work meets play with ease at over 4,040 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

More from Airbnb

Airbnb experiences

Experience something new

Airbnb services

Make your stay more special

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee