Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Cottage in Kissimmee
4.98 out of 5 average rating, 134 reviewsRunaway 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
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy 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.
Aug 27 – Sep 3
Apartment in Kissimmee
4.92 out of 5 average rating, 200 reviewsModern 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
Nov 16 – 23
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee vacation rentals
Vacation rentals with pools in Kissimmee
Guest suite in Kissimmee
4.83 out of 5 average rating, 501 reviewsPrivate 2 bedroom w/bathrm in portion of POOL home
Dec 29 – Jan 5
Tiny home in Kissimmee
4.95 out of 5 average rating, 142 reviewsDisney Tiny House Getaway!
Oct 2 – 9
Condo in Kissimmee
4.98 out of 5 average rating, 283 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Feb 7 – 14
Home in Kissimmee
4.9 out of 5 average rating, 290 reviewsFamily Home minutes from Disney!
Aug 4 – 11
Tiny home in Kissimmee
4.94 out of 5 average rating, 326 reviewsBlue Bungalow Tiny House near all Attractions!!
Mar 1 – 8
Home in Kissimmee
4.84 out of 5 average rating, 204 reviews3 bedroom Villa in Kissimmee
Mar 9 – 16
Tiny home in Kissimmee
4.9 out of 5 average rating, 433 reviewsZMZ Tiny House Living! Try it out while at Disney
Mar 4 – 11
Townhouse in Kissimmee
4.96 out of 5 average rating, 158 reviewsBE OUR GUEST! Close to Disney and Universal - Pool
Sep 4 – 11
Condo in Kissimmee
4.94 out of 5 average rating, 180 reviewsLakeview escape close to Disney&retail therapy
Mar 20 – 27
Condo in Kissimmee
4.85 out of 5 average rating, 155 reviewsBeautiful Resort-Style Condo with Waterpark!
Oct 13 – 20
Condo in Kissimmee
4.96 out of 5 average rating, 149 reviewsWelcome to our Son Shine condo ....
Mar 19 – 26
Cottage in Kissimmee
4.9 out of 5 average rating, 203 reviewsBe Our Guest Sandcastle Cottage 81
Nov 1 – 8
Homes for rent in Kissimmee
Home in Kissimmee
4.94 out of 5 average rating, 251 reviewsCozy renovated older home near Disney
Apr 18 – 25
Home in Davenport
4.8 out of 5 average rating, 133 reviewsNew Listing : Sonja's Serenity home with pool
Aug 19 – 26
Home in Kissimmee
4.87 out of 5 average rating, 154 reviewsCharming 3-Bedroom Home: 25 Mins from Disney!
Sep 23 – 30
Home in St. Cloud
4.97 out of 5 average rating, 153 reviewsCozy and Quiet studio Miles from Major attractions
Jan 20 – 27
Home in Kissimmee
4.9 out of 5 average rating, 105 reviewsCozy Kissimmee home 3BR/2Bath near Orlando Airport
Aug 2 – 9
Home in Kissimmee
4.89 out of 5 average rating, 176 reviewsJacuzzi-3BR-HeatedRESORTpool,HBO,WiFi-7mlsDisney
Jun 2 – 9
Home in Kissimmee
4.96 out of 5 average rating, 227 reviewsSo close to Disney you can feel the magic!
Sep 16 – 23
Home in Orlando
4.91 out of 5 average rating, 171 reviewsDowntown Orlando-Harwood House-Lake Eola-Historic
May 17 – 24
Home in Davenport
4.86 out of 5 average rating, 117 reviewsDisney getaway
Oct 23 – 30
Home in Kissimmee
4.92 out of 5 average rating, 123 reviewsSouth Facing Pool Home! 5 Miles from Disney
May 10 – 17
Home in Kissimmee
4.83 out of 5 average rating, 113 reviewsAgradable casa, en comunidad privada, con piscina
Nov 26 – Dec 3
Home in Kissimmee
4.83 out of 5 average rating, 241 reviewsNew Home Next To Disney!
Jul 14 – 21
Villas for rent in Kissimmee
Villa in Davenport
4.94 out of 5 average rating, 108 reviewsBeautiful 4 Bedroom Pool Villa Near Disney World
Sep 13 – 20
Villa in Kissimmee
4.79 out of 5 average rating, 158 reviewsClaudia's Casita 15 min to Disney
May 15 – 22
Villa in Kissimmee
4.96 out of 5 average rating, 165 reviews4 bed villa w/private pool near Disney, sleeps 6+
Aug 21 – 28
Villa in Kissimmee
4.99 out of 5 average rating, 148 reviewsDisney-Themed Home w/ Game Room & Private Hot Tub!
Sep 16 – 23
Villa in Kissimmee
4.87 out of 5 average rating, 141 reviewsMinutes from Disney Gated LakeView Pvt Heated Pool
Nov 15 – 22
Villa in Kissimmee
4.97 out of 5 average rating, 126 reviewsClose To The Mouse: Something for Everyone!
May 31 – Jun 7
Villa in Kissimmee
4.84 out of 5 average rating, 367 reviewsAmazing Cozy 4Bed/3Bath, Disney Area, Private Pool
Nov 12 – 19
Villa in Kissimmee
4.78 out of 5 average rating, 400 reviews7BD with Movie Theater Pool & Jacuzzi near Disney!
Jan 14 – 21
Villa in Kissimmee
4.87 out of 5 average rating, 110 reviewsLuxury 9 bedrooms house nearby DISNEY 27
Apr 6 – 13
Villa in Kissimmee
4.91 out of 5 average rating, 117 reviewsWaterfront Retreat,King Bed,Heated Pool & Fire Pit
Mar 14 – 21
Villa in Kissimmee
4.81 out of 5 average rating, 58 reviewsSpacious family friendly Disney vacation home
May 17 – 24
Villa in Davenport
4.88 out of 5 average rating, 49 reviewsGorgeous 3 bed, 2 bath villa w/ pool and jacuzzi
Jan 11 – 18
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.
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