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Vacation rentals in Kissimmee

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Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

Kissimmee Lakefront Park137 locals recommend
Kissimmee Gateway Airport8 locals recommend
Gatorland412 locals recommend

Private vacation rentals in Kissimmee

Guest favorite
Villa in Kissimmee
4.83 out of 5 average rating, 72 reviews

Home w/ PVT Pool, Game Room & Resort access

ValerieRating, 5 stars2 weeks ago
My whole family loved this house and everything about it. We will definitely stay again on our next trip.
Superhost
The kitchen area features a spacious island with modern appliances and seating for three. Adjacent to the kitchen are two lounge chairs and a small side table, creating a cozy seating area. Natural light brightens the open layout, highlighting the elegant tile flooring.
Home in Davenport
5 out of 5 average rating, 4 reviews

Villa 4BD in Champions Gate for 8 – Private Pool

JoaquimRating, 5 stars5 months ago
Edney was a fantastic host! He made everything easy with clear and friendly communication, ensuring we had everything we needed for a stress-free stay. The house was amazing – spotless, roomy, and thoughtfully decorated, with every detail carefully considered. It completely surpassed our expectations! We would highly recommend staying here and look forward to coming back someday. Thank you, Edney, for an outstanding experience!
Guest favorite
An aerial view showcases a vibrant community with colorful villas bordering a serene lake. A pool area is complemented by palm trees, sun loungers, and shaded cabanas. Leisure spaces invite relaxation, while the surrounding greenery adds a touch of nature to the resort environment.
Vacation home in Kissimmee
4.83 out of 5 average rating, 104 reviews

Magical & Cozy Home - Runaway Resort near Disney

Olga LuciaRating, 5 stars5 months ago
Everything was excellent! Especially the host's attention, she is ready to help, she responds quickly. It is close to Disney parks, supermarket, restaurants, gas station.
Guest favorite
A dining area features several wooden tables and comfortable black chairs. Set for breakfast, the tables display white dishware and glassware. A bar area with stools is visible in the background, along with shelves containing various beverages.
Townhouse in Kissimmee
4.94 out of 5 average rating, 190 reviews

Beautiful family home near all attractions.

KatannaRating, 5 stars5 days ago
Super attentive and helpful. Very kind. Allowed a late checkout to help me accommodate my changed flight. Comfortable. Felt safe.
Guest favorite
A Mickey Mouse-shaped waffle maker is shown with a waffle in the shape of Mickey Mouse partially cooked inside. Two golden-brown Mickey Mouse waffles sit on a white plate in front of the appliance, highlighting their playful design.
Home in Kissimmee
4.88 out of 5 average rating, 250 reviews

Private Heated Pool & Hot Tub; 6 miles to Disney

KellyRating, 5 stars1 month ago
This is our second time at this house and we enjoyed the space just as much as the first time. Will be coming back again for sure
Guest favorite
A games room is shown featuring a pool table and an air hockey table. The space is complemented by a washer and dryer set against a wall, with additional storage shelves above. The floor is finished in a smooth, grey coating.
Home in Kissimmee
4.89 out of 5 average rating, 192 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

AustinRating, 5 stars3 weeks ago
Another great stay here!
Superhost
Home in Four Corners
4.86 out of 5 average rating, 51 reviews

Luxury Pool Home Near Disney

JustineRating, 5 stars3 weeks ago
We had an amazing stay, the place was centrally located but out of the hustle and bustle of traffic. We were able to get to Disney and ESPN center fairly fast. The townhouse was much bigger than anticipated. Absolutely would stay here again.
Guest favorite
The entrance features a dark green front door with a paneled design, complemented by a small window above it. The door is framed by light green walls, and a neatly maintained shrub is positioned on either side of the doorway.
Townhouse in Kissimmee
4.81 out of 5 average rating, 70 reviews

Entire Townhouse -Kissimmee, 4 Bedrooms 3 Bath

VanessaRating, 5 stars3 months ago
Cármen is an excellent host! The house is a grace, very well equipped, the condominium is complete. In addition, it is very close to Disneyland. We love it, we'll definitely be back!

Pet-friendly vacation rentals in Kissimmee

Guest favorite
The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.
Cottage in Kissimmee
4.98 out of 5 average rating, 113 reviews

1BD Cottage "Limoncello" in Margaritaville

PegRating, 5 stars1 month ago
Daniel’s place was perfect for our excursions to Disney & Universal studios. He was quick to answer with any questions we had & there were a lot of choices of various restaurants in the area.
Guest favorite
A cozy living area features comfortable seating and a flat-screen TV, complemented by light streaming in through white blinds. A well-equipped kitchen is visible in the background, and an inviting bedroom with a king bed is seen alongside a detached private sauna, surrounded by lush greenery.
Cottage in Orlando
4.94 out of 5 average rating, 141 reviews

Mills Lakeside

MarkRating, 5 stars1 month ago
Great place to stay! Beautiful property, would stay here again.
Guest favorite
A bright living area features a light-colored couch with decorative cushions, a patterned armchair, and a wooden coffee table. Natural light enters through large windows adorned with blinds. A ceiling fan hovers above, and a potted plant adds a touch of greenery.
Apartment in Kissimmee
4.92 out of 5 average rating, 119 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

TyronnRating, 5 stars1 week ago
Very pleasant and worth the stay! Our host was very responsive and helpful. The area we stayed was also quiet which was also a good thing. Also the location is so close to so many stores, restaurants and parks. I will be visiting again
Superhost
A spacious bedroom features a large bed with white linens, complemented by bedside tables with lamps. A ceiling fan is mounted above, and large windows with elegant curtains allow natural light to illuminate the room. A decorative globe and a bench provide additional accents.
Condo in Kissimmee
5 out of 5 average rating, 3 reviews

Pet Friendly Reunion Condo Minutes from Disney!

HeatherRating, 5 stars4 months ago
Amazing little spot if you are in the Orlando area. Pristine air b&b. I walked into a freshly clean condo with soft music playing on the tv, lights turned on and a plate of snack waiting for me. Communication was wonderful and the door was peaceful and homey. Absolutely would stay here again.
Guest favorite
The image displays a modern home with a private pool, surrounded by a screened enclosure. Lounge chairs are positioned near the inviting water, reflecting the soft hues of sunset. A well-maintained exterior showcases a spacious driveway and lush grass, inviting guests to relax and enjoy.
Home in Kissimmee
4.85 out of 5 average rating, 175 reviews

Close to Disney!

HaleyRating, 5 stars3 days ago
We had a great stay here, the kids loved the pool, and everything was clean.
Guest favorite
A comfortable living area features a gray sofa, a sleek coffee table, and a television. Natural light fills the space through the sliding glass door that leads to a walkout balcony, which is furnished with chairs and offers views of the surrounding landscape.
Condo in Orlando
4.79 out of 5 average rating, 178 reviews

Amazing Pet-Friendly 3BR condo near Epic Universe!

JordanRating, 5 stars1 month ago
The space was perfect for my family. We enjoyed the pool and location was perfect for stores, and near the convention center where my daughter had a competition. Great communication with host was quick to respond.
Superhost
The exterior of a newly remodeled mobile home is shown, featuring a covered porch with steps leading to the entrance. Soft green grass and a palm tree add to the inviting appearance, while nearby trees provide a natural backdrop. The home is set in a mobile home park.
Home in Orlando
4.63 out of 5 average rating, 56 reviews

NEWLY remodeled PET FRIENDLY 2br/1bath by OIA

OlgaRating, 5 stars3 months ago
We really liked being there, it is a very quiet place and the communication with our host was excellent, any inconvenience that was presented to us, he quickly solved it.
Superhost
An outdoor seating area features a dining table surrounded by teal chairs, inviting relaxation. String lights illuminate the space, which overlooks a swimming pool and lush greenery. A cozy double hammock is positioned nearby, contributing to a peaceful ambiance during sunset.
Home in Kissimmee
4.72 out of 5 average rating, 96 reviews

Southwest facing pool! 5 Miles from Disney.

LauraRating, 5 stars2 months ago
Everything was great! We had a few glitches, but the host was very quick to sort them out. The only thing I think the host needs to change is the heating of the pool, sometimes when we were late getting back from the city, we wanted to get into the jacuzzi after 9 p.m., because the heating of the pool was from 9 a.m. to 9 p.m.

Homes in Kissimmee

Superhost
A spacious living area is showcased, featuring a wooden coffee table in the center and a TV mounted on a dark wooden entertainment unit. A sofa and armchair are arranged around the table. The dining area can be seen in the background, furnished with a round table and high chairs.
Home in Four Corners
4.78 out of 5 average rating, 100 reviews

Jas Vacation Home

EltonRating, 5 stars1 month ago
We had everything we needed and enjoyed our stay. It was the perfect location and setting for our family. The only thing I can suggest is getting the back gate fixed so it latches.
Top guest favorite
A private pool area is showcased, featuring a clear blue pool surrounded by a screened enclosure. Comfortable lounge chairs in turquoise are positioned beside the pool. A serene pond and lush greenery are visible beyond the enclosure, providing a calm backdrop.
Home in Kissimmee
4.93 out of 5 average rating, 138 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

IanRating, 5 stars1 month ago
Nice place and a great location. The villa is ideal for a lovely holiday to Orlando and in an ideal location with a lake behind and very scenic. Would return again and Jeff is a great host.
Guest favorite
A modern home features a sparkling pool surrounded by lounge chairs and shaded seating areas. The exterior showcases a neat two-story design with light-colored siding and landscaped greenery. Interior views include a fully equipped kitchen with stainless steel appliances and a cozy bedroom with a large bed and natural light.
Home in Kissimmee
4.96 out of 5 average rating, 25 reviews

Beautiful Gated Home near Disney and Universal

GeenaRating, 5 stars2 weeks ago
Our stay was great ! Everything was exactly as described. The beds are super comfy and the whole house was clean and tidy. Our host sent clear instructions and our stay was smooth . Would absolutely book again ! Thank you !!
Superhost
An engaging Star Wars-themed game room features a foosball table, arcade machines, and a spacious seating area. Murals depict scenes from the franchise, with screens displaying games. The room is designed for fun and entertainment, offering a vibrant environment for guests.
Home in Kissimmee
4.83 out of 5 average rating, 139 reviews

Orlando Home with Private Pool & Game Room !

JohnRating, 5 stars1 month ago
We had an awesome stay! The house was incredibly spacious. The location was perfect— close to everything including the Disney parks. There are also many food options close by. The kids loved the game room and pool. I would recommend staying in this home.
Guest favorite
A spacious living area is furnished with a blue sofa and two green accent chairs. A glass coffee table sits on a patterned rug, surrounded by decorative plants. Light filters through windows with patterned curtains, creating a bright and inviting atmosphere.
Home in Orlando
4.88 out of 5 average rating, 114 reviews

Modern Home near DT&Airport/Community Pool Nearby

HeidiRating, 5 stars1 month ago
we had a wonderful stay in Orlando house was spacious and only 20 minutes from UCF where our daughter was the house looked just like the photos. very comfortable and lots of towels! everything we needed I kitchen. host was extremely responsive which is important!
Guest favorite
A vibrant water play area features a colorful pirate ship surrounded by palm trees and outdoor lounge seating. A slide extends from the ship into a shallow splash zone, inviting family fun. Bright umbrellas provide shade in the background, enhancing the lively atmosphere.
Home in Davenport
5 out of 5 average rating, 18 reviews

New Family friendly townhome.

Jean-FrancoisRating, 5 stars2 months ago
Very pleasant stay, proactive host and always attentive. To be noted for a future visit.
Guest favorite
Home in Kissimmee
4.89 out of 5 average rating, 27 reviews

Spacious 5BR Villa with Pool, Close to Disney Fun!

DamianRating, 5 stars1 month ago
Stayed here as a family and was lovely, everything you needed and kids loved the pool. The house was clean, kirstie was very responsive to all questions and any issues. Would definitely recommend and use again. Thank you! 😁
Superhost
The exterior of the villa features a light-colored facade with a distinctive archway entrance and blue front door. Lush greenery surrounds the entrance, and palm trees are visible, adding to the welcoming feel. A paved driveway leads up to the home.
Home in Davenport
4.84 out of 5 average rating, 135 reviews

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes

PatRating, 5 stars2 weeks ago
Awesome place! Absolutely loved our stay! Will definitely go back next time in Florida.

Quick stats about vacation rentals in Kissimmee

  • Total rentals

    7.2K properties

  • Total number of reviews

    242K 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

    6.5K properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

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 490 apartment rentals, over 3,470 house rentals to over 740 villa 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 3,930 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
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  3. Florida
  4. Osceola County
  5. Kissimmee