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Vacation rentals in Kissimmee

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

The Hideaway Club House at Storey Lake5 locals recommend
Kissimmee Lakefront Park171 locals recommend
Silver Spurs Arena9 locals recommend
Kissimmee Gateway Airport4 locals recommend
Gatorland417 locals recommend
Loop West Shopping Center256 locals recommend

Private vacation rentals in Kissimmee

Superhost
The open-concept kitchen and living area feature modern appliances and sleek countertops. Bar stools provide seating at the kitchen island, and a dining table accommodates six. Natural light fills the space, highlighting the blue accent wall and comfortable seating in the living area.
Home in Davenport
5 out of 5 average rating, 4 reviews

Villa 4BD in Champions Gate for 8 – Private Pool

JoaquimRating, 5 stars4 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!
Superhost
A private pool is surrounded by a screened enclosure, capturing the evening sky's colors. Natural light filters through the adjacent glass doors, revealing a dining area with patio seating nearby. The tranquil water surface reflects the vibrant hues of sunset.
Home in Kissimmee
4.83 out of 5 average rating, 6 reviews

Cute Vacation Home Very Close to Disney

T LianneRating, 5 stars3 months ago
We really enjoyed the house and pool. It was very convenient to parks and shopping /restaurants.
Superhost
An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

ChrisRating, 5 stars3 weeks ago
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!
Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Vacation home

JaniquaRating, 5 stars3 weeks ago
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate
Guest favorite
Vacation home in Kissimmee
4.83 out of 5 average rating, 104 reviews

Nice & Cozy Home near Disney

Olga LuciaRating, 5 stars3 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 clear no smoking sign is displayed on the door, emphasizing a strict no smoking policy, including e-cigarettes. Through the window, a glimpse of the private heated pool can be seen, surrounded by trees and landscaped areas.
Home in Kissimmee
4.88 out of 5 average rating, 246 reviews

Private Heated Pool & Hot Tub; 6 miles to Disney

JillianRating, 5 stars2 weeks ago
Bobbie was super helpful and responded quickly! The hot tub and pool were great and the Mickey motif was perfect! We had a great time and plenty of room. The pool table and pop a shot were an added bonus for the evenings after Disney and Universal! Great time and a great price! Thank you, Bobbie!
Guest favorite
A private pool area is enclosed with mesh screening, featuring clear blue water. Two lounge chairs are positioned beside the pool on a sunlit patio. A view of a grassy area and trees is visible through the enclosure.
Home in Kissimmee
4.88 out of 5 average rating, 188 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

MustafaRating, 5 stars2 weeks ago
Great house and host was very friendly with clear instructions on check in and check out. Pool was clean and well maintained.
Superhost
Home in Four Corners
4.88 out of 5 average rating, 48 reviews

H2412T-Windsor at Westside Resort/POOL/Water Park

EdwardRating, 5 stars5 days ago
Very nice place my family and I enjoyed staying at Michael’s place, the only thing I dislike was the fact that is too close to the Disney parks and coming back to the place after being out the traffic is kind of heavy but there is nothing anyone can do about that, Love the place!! Thank you Michael!!.

Pet-friendly vacation rentals in Kissimmee

Top guest favorite
A spacious pool area features a large swimming pool surrounded by comfortable lounge chairs and a hot tub. The hot tub bubbles gently, and the area is enclosed by a screened patio, providing privacy and protection from insects.
Home in Kissimmee
4.92 out of 5 average rating, 133 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

AshleyRating, 5 stars1 month ago
We had a great spring break trip here! My boys loved the pool and game room! Well worth the money! Location was great close to food, shopping and Disney! Highly recommend this place for families! The hosts are super helpful and friendly!
Top guest favorite
A charming exterior of a two-story home showcases a welcoming entrance with a lit doorway. Lush greenery, including palm trees, frames the path leading up to the door. The warm exterior is highlighted by soft illumination, creating an inviting atmosphere.
Townhouse in Kissimmee
5 out of 5 average rating, 12 reviews

MY HAPPY PLACE 5 Near Celabration and Disney

GlendaRating, 5 stars4 days ago
Love the place, felt right at home. Wish we had more private access to the pool like if it was in the backyard but overall the place was lovely. Love that everyone has their own space and bathroom. She was very responsive. Although was very dry in her responses she definitely answered everything very proactive. Would Definitely stay there 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
4.91 out of 5 average rating, 110 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

PatrycjaRating, 5 stars3 weeks ago
I recommend this place. It was easy to find, easy check-in. Host always responsed to my texts, even the silly ones :) The apartment is specious. It was very clean and had lots of towels.
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
4.88 out of 5 average rating, 166 reviews

Close to Disney!

CameronRating, 5 stars4 days ago
Sarah was a very engaging and responsive host. My family enjoyed the place, the kids loved playing pool and swimming in the pool. Would definitely recommend
Superhost
A spacious bedroom is presented with a king-sized bed adorned with decorative pillows. Elegant curtains frame a window, allowing natural light to enhance the warm tones of the room. An accent chair and lamp are positioned beside the bed, contributing to a cozy ambiance.
Villa in Kissimmee
5 out of 5 average rating, 3 reviews

Westgate Resort/Water Park Onsite Included

Kristal Rating, 5 stars12 months ago
Octavia was wonderful. She was always responsive. We loved our room and our stay.
Superhost
A spacious living area features a comfortable sectional sofa and a coffee table. A fully equipped kitchenette can be seen in the background. Wall-mounted big smart TV displays streaming service icons, and a dining table is positioned nearby. The decor is neutral and inviting, with natural light coming from the window.
Apartment in Kissimmee
4.74 out of 5 average rating, 109 reviews

Family Disney Universal Orlando

MelanieRating, 5 stars2 weeks ago
Host was responsive all the time, she made me and my family feel like home, the place was very clean and accessible, address was clear and she helped me with everything, hope I can visit this place again soon !!
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 stars2 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 stars3 weeks 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 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, 136 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

AmandaRating, 5 stars3 months ago
We had such an enjoyable time here. We highly recommend it to all. The pool was a huge winner for our kids and the location was perfect. Thanks again!
Superhost
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews

Beautiful Gated Home near Disney and Universal

BenejahRating, 5 stars3 weeks ago
My stay was amazing I will be booking again
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, 136 reviews

Orlando Home with Private Pool & Game Room !

TammyRating, 5 stars2 weeks ago
This was the perfect place to stay for our family vacation. The kids loved the game room and the pool. The house was clean and in a nice, safe neighborhood. Our host was very polite and very responsive. We loved every minute of our stay and we would definitely stay here again. Highly recommend!!
Superhost
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 stars1 month ago
Very nice stay, proactive host and always attentive. To keep in mind for a future visit.
Superhost
A large two-story home is showcased with a well-maintained lawn and framed by palm trees. The exterior features a mix of light and dark colors, with a welcoming front porch and bright exterior lights. A driveway leads to a spacious garage, enhancing the home's curb appeal.
Home in Davenport
4.77 out of 5 average rating, 114 reviews

There is no other place you want to be than here.

ChrisRating, 5 stars2 days ago
We’ve just finished a fantastic family holiday at this villa and can’t recommend it highly enough. The house was spotless on arrival, with plenty of fresh towels and hotel‑quality linen. The open‑plan living area is bright and welcoming, and the kitchen has every utensil you could possibly need—including a decent sharp knife (rare in rentals!). The private pool is the real star: perfectly clean, comfortably heated, and enclosed for peace of mind with younger children. Location‑wise, it’s an easy drive to Disney and Universal, but far enough away to escape the crowds; supermarkets and restaurants are only a few minutes up the road. Communication with Frank was first‑class from booking to check‑out—quick replies and genuinely helpful advice. If you’re after a stress‑free, family‑friendly base in the Orlando area, book this place—you won’t be disappointed.
Superhost
Home in Kissimmee
4.96 out of 5 average rating, 24 reviews

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

TravisRating, 5 stars1 month ago
This is overall a nice place in a gated community. The home is large and the amenities are great. A short 2 block walk to the community center pool with small waterpark was also really nice especially for kids.
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, 134 reviews

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes

JosephRating, 5 stars1 week ago
Luis was a very responsive host, we had small issues throughout 8 week stay and he always replied quickly and got things handled. A large part of our time there included us having our 88 year old mother with us and it was very satisfying to have Luis follow through on his promises for the pool heat level and air conditioning level at night so she could sleep comfortably. The house suited our family very well with 5 bedrooms and 4 washrooms, 3 of the bedrooms included ensuites. The pool was part of the highlight with sun shining usually from 11am to 6pm. Overall we were quite satisfied with our choice
Superhost
The entrance of a gated community is framed by tall palm trees against a clear blue sky. Decorative stone pillars mark the entryway, with lush greenery and vibrant landscaping visible along the driveway. Cloud formations add texture to the scenic backdrop.
Home in Davenport
4.83 out of 5 average rating, 101 reviews

Family Home Gated 10 Beds Pool Disney 7 miles.

SamanthaRating, 5 stars1 week ago
Great stay! The place was clean, comfortable, and exactly as described. Roy was very responsive and made check-in super easy. Would definitely recommend and stay again!

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 3,470 house rentals, over 740 villa rentals to over 490 apartment 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
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee