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Vacation rentals in Kissimmee

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Kissimmee

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 134 reviews

Runaway Beach Club Private Patio:Disney, Universal

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Sep 11 – 18

G$27,084 GYD per night
Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 164 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Nov 18 – 25

G$23,094 GYD per night
Guest favorite

Apartment in Kissimmee

4.92 out of 5 average rating, 200 reviews

Modern APT W/ Patio 15 mins from Theme Parks & MCO

Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado

Jun 6 – 13

G$26,197 GYD per night

Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

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

Vacation rentals with pools in Kissimmee

Guest favorite

Home in Kissimmee

4.84 out of 5 average rating, 204 reviews

3 bedroom Villa in Kissimmee

Sep 23 – 30

G$25,093 GYD per night
Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 111 reviews

First floor/your Disney escape

Sep 18 – 25

G$23,067 GYD per night
Guest favorite

Condo in Kissimmee

4.98 out of 5 average rating, 283 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Aug 22 – 29

G$27,777 GYD per night
Guest favorite

Cottage in Kissimmee

4.94 out of 5 average rating, 364 reviews

Entire Cottage close to Disney, Universal, Airport

Jun 11 – 18

G$20,328 GYD per night
Guest favorite

Vacation home in Orlando

4.82 out of 5 average rating, 100 reviews

The Lovers Haven (Romantic Studio w/ Balcony)

Sep 12 – 19

G$23,069 GYD per night
Guest favorite

Tiny home in Kissimmee

4.9 out of 5 average rating, 433 reviews

ZMZ Tiny House Living! Try it out while at Disney

Sep 18 – 25

G$18,291 GYD per night
Guest favorite

Tiny home in Kissimmee

4.95 out of 5 average rating, 142 reviews

Disney Tiny House Getaway!

Apr 29 – May 6

G$19,336 GYD per night
Guest favorite

Guest suite in Kissimmee

4.83 out of 5 average rating, 501 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Jul 2 – 9

G$15,783 GYD per night
Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 117 reviews

Beautiful studio with pool & close to attractions!

May 28 – Jun 4

G$18,127 GYD per night
Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 149 reviews

Welcome to our Son Shine condo ....

Oct 22 – 29

G$28,927 GYD per night
Guest favorite

Townhouse in Kissimmee

4.91 out of 5 average rating, 130 reviews

☀️THE☀️SUNSHINE☀️HOUSE☀️(3BD/2BA/3SmartTVs)☀️

Sep 15 – 21

G$19,587 GYD per night
Guest favorite

Townhouse in Kissimmee

4.96 out of 5 average rating, 157 reviews

BE OUR GUEST! Close to Disney and Universal - Pool

Jul 9 – 16

G$26,388 GYD per night

Homes for rent in Kissimmee

Guest favorite

Home in Kissimmee

4.96 out of 5 average rating, 227 reviews

So close to Disney you can feel the magic!

May 11 – 18

G$30,167 GYD per night
Guest favorite

Home in Kissimmee

4.94 out of 5 average rating, 251 reviews

Cozy renovated older home near Disney

Sep 1 – 8

G$24,103 GYD per night
Guest favorite

Home in Kissimmee

4.9 out of 5 average rating, 105 reviews

Cozy Kissimmee home 3BR/2Bath near Orlando Airport

Apr 26 – May 3

G$31,769 GYD per night
Guest favorite

Home in Kissimmee

4.87 out of 5 average rating, 154 reviews

Charming 3-Bedroom Home: 25 Mins from Disney!

May 4 – 11

G$23,194 GYD per night
Superhost

Home in Kissimmee

4.83 out of 5 average rating, 240 reviews

New Home Next To Disney!

Aug 2 – 9

G$26,466 GYD per night
Guest favorite

Home in Clermont

4.99 out of 5 average rating, 153 reviews

Clermont Cottage Near the Lake

Sep 14 – 21

G$25,761 GYD per night
Guest favorite

Home in St. Cloud

4.97 out of 5 average rating, 153 reviews

Cozy and Quiet studio Miles from Major attractions

Dec 4 – 11

G$15,505 GYD per night
Guest favorite

Home in Orlando

4.91 out of 5 average rating, 171 reviews

Downtown Orlando-Harwood House-Lake Eola-Historic

Oct 6 – 13

G$23,560 GYD per night
Guest favorite

Home in Orlando

4.82 out of 5 average rating, 125 reviews

The Comfy Milk District Home | Downtown |

Sep 11 – 18

G$17,060 GYD per night
Guest favorite

Home in Kissimmee

4.89 out of 5 average rating, 176 reviews

Jacuzzi-3BR-HeatedRESORTpool,HBO,WiFi-7mlsDisney

Jun 2 – 9

G$26,329 GYD per night
Superhost

Home in Kissimmee

4.83 out of 5 average rating, 113 reviews

Nice house, private community, with pool

Sep 11 – 18

G$31,412 GYD per night
Guest favorite

Home in Davenport

4.95 out of 5 average rating, 157 reviews

DOLPHIN COVE NEAR DISNEY

Sep 24 – Oct 1

G$30,048 GYD per night

Villas for rent in Kissimmee

Guest favorite

Villa in Kissimmee

4.96 out of 5 average rating, 165 reviews

4 bed villa w/private pool near Disney, sleeps 6+

Sep 9 – 16

G$31,967 GYD per night
Superhost

Villa in Kissimmee

4.87 out of 5 average rating, 141 reviews

Minutes from Disney Gated LakeView Pvt Heated Pool

Nov 15 – 22

G$35,772 GYD per night
Guest favorite

Villa in Davenport

4.94 out of 5 average rating, 108 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

Aug 25 – Sep 1

G$38,572 GYD per night
Guest favorite

Villa in Kissimmee

4.99 out of 5 average rating, 148 reviews

Disney-Themed Home w/ Game Room & Private Hot Tub!

Jan 31 – Feb 7

G$78,851 GYD per night
Guest favorite

Villa in Kissimmee

4.79 out of 5 average rating, 158 reviews

Claudia's Casita 15 min to Disney

Aug 1 – 8

G$36,209 GYD per night
Guest favorite

Villa in Kissimmee

4.84 out of 5 average rating, 367 reviews

Amazing Cozy 4Bed/3Bath, Disney Area, Private Pool

Nov 12 – 19

G$40,540 GYD per night
Guest favorite

Villa in Kissimmee

4.92 out of 5 average rating, 178 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Sep 9 – 16

G$68,928 GYD per night
Guest favorite

Villa in Kissimmee

4.97 out of 5 average rating, 126 reviews

Close To The Mouse: Something for Everyone!

Feb 24 – Mar 3

G$42,576 GYD per night
Guest favorite

Villa in Kissimmee

4.78 out of 5 average rating, 400 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

Jan 14 – 21

G$71,054 GYD per night
Guest favorite

Villa in Kissimmee

4.91 out of 5 average rating, 116 reviews

Waterfront Retreat,King Bed,Heated Pool & Fire Pit

Feb 22 – Mar 1

G$62,873 GYD per night
Guest favorite

Villa in Davenport

4.88 out of 5 average rating, 49 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Jan 15 – 22

G$32,383 GYD per night
Superhost

Villa in Davenport

4.93 out of 5 average rating, 29 reviews

Spectacular 3b/2b With Private Pool And Spa

Sep 5 – 12

G$32,434 GYD per night

Quick stats about vacation rentals in Kissimmee

Total rentals

7.6K properties

Rentals with dedicated workspaces

3.9K properties have a dedicated workspace

Rentals with a pool

6.8K properties have a pool

Pet-friendly rentals

1.1K properties allow pets

Family-friendly rentals

6.6K properties are a good fit for families

Total number of reviews

197K reviews

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.


The best time to stay in a vacation rental in Kissimmee

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.


Top things to do in Kissimmee

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

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 900 villa rentals to over 3,520 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 3,900 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