Vacation rentals in Kissimmee

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Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Medieval Times Dinner & Tournament346 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend
Walmart Supercenter44 locals recommend

Other great vacation rentals in Kissimmee

Guest favorite

Condo in Kissimmee

4.92 out of 5 average rating, 262 reviews

Beautiful Beach Style Condo minutes from Disney

Nov 14 – 21

G$20,916 GYD per night
Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 110 reviews

Modern Storey Lake Resort Disney Orlando 3171-206

Sep 18 – 25

G$27,732 GYD per night
Guest favorite

Apartment in Kissimmee

5.0 out of 5 average rating, 5 reviews

Stylish Retreat w/ 2 Queen Beds-Pool-Gym-Game Room

Apr 16 – 23

G$19,593 GYD per night
Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 16 reviews

Disney Retreat

Nov 13 – 20

G$21,625 GYD per night
Guest favorite

Townhouse in Kissimmee

5.0 out of 5 average rating, 10 reviews

Summer Studio at Kissimmee

Jul 4 – 11

G$18,611 GYD per night
Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 51 reviews

Cozy Orlando Area Cottage - 4 Miles to Disney

Nov 5 – 12

G$22,411 GYD per night
Guest favorite

Home in Kissimmee

5.0 out of 5 average rating, 63 reviews

Villa by the Lakes

Jul 9 – 16

G$26,041 GYD per night
Superhost

Apartment in Kissimmee

4.8 out of 5 average rating, 103 reviews

King Bed, Great Amenities, and Disney Calling You

May 7 – 14

G$23,154 GYD per night

Quick stats about vacation rentals in Kissimmee

Total rentals

7.3K properties

Rentals with dedicated workspaces

3.6K properties have a dedicated workspace

Rentals with a pool

6.6K properties have a pool

Pet-friendly rentals

1K properties allow pets

Family-friendly rentals

6.3K properties are a good fit for families

Total number of reviews

206K reviews

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 450 apartment rentals, over 870 villa rentals to over 3,300 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 3,620 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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