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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

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

Private vacation rentals in Kissimmee

Top guest favorite
A sleek coffee table is highlighted with a reflective surface, displaying an arrangement of four black decorative bowls. A modern white armchair with a deep blue cushion is positioned beside the table, contributing to a sophisticated living area. Soft natural light filters through nearby sheer curtains.
Home in Kissimmee
4.92 out of 5 average rating, 12 reviews

Gorgeous 5BR @Encore next to Disney - 7710

StephanieRating, 5 stars3 weeks ago
This home is great, nicely kept and has enough space for everyone with the bedrooms well appointed and 3 king beds - hard to find with AirBnb, most have multiple beds trying to maximize their space, but this place is perfect with a bathroom for each room and privacy in the backyard. Amazing heated pool and jacuzzi and kid and dog friendly! Definitely worth the money, great location and everything you need. Thanks Frank! 💫
Superhost
Home in Kissimmee
5 out of 5 average rating, 4 reviews

4561 Majestic 9BD Kingdom Retreat Near Disney

RadajiaRating, 5 stars4 weeks ago
BOOK IT! The home looks exactly like pictures. It was plenty room for my family and the kids was so entertained with ball pits, slide, pool and game room that we didn’t have to leave the house for entertainment. I love that it was plenty unlimited parking unlike other places I booked. They had a lots of dishes, glasses and utensils available also. They had fast responses and handled all request in a timely fashion. The pool heater was set to perfect temperature. I request it to be set 70 degrees and someone came out and adjusted quickly. My family and I will 100% be back!
Guest favorite
A serene outdoor space features a clear swimming pool under soft evening light. A BBQ grill is situated next to a fire table, which provides a warm glow. The area is enclosed with screens, enhancing privacy while enjoying the inviting atmosphere.
Home in Davenport
4.93 out of 5 average rating, 82 reviews

Sweet vacation home.

TatianaRating, 5 stars2 months ago
It was an extremely nice getaway, felt like a home away from home! They were very responsive and helpful. Couldn’t have been better!!
Superhost
Home in Kissimmee
4.76 out of 5 average rating, 76 reviews

Short Drive to Disney Pool + Spa

PablianaRating, 5 stars1 week ago
Osiris responded quickly. The house is just like the photos, very beautiful and with plenty of space, the pool is at the perfect temperature and it is close to Walmart , near to Disney park. I recommend it!!
Top guest favorite
An outdoor patio area is showcased, featuring comfortable seating with blue cushions arranged around a low table. A geometric rug is laid on the floor, and the fenced-in pool area is visible, complete with floating pool toys and surrounding greenery.
Home in Kissimmee
5 out of 5 average rating, 24 reviews

Amazing Pool, Large, Clean & Private Home, by Anel

JenniferRating, 5 stars1 month ago
We really enjoyed this house. It was very clean and the pool and privacy with the fenced in yard was really nice!
Top guest favorite
Home in Kissimmee
4.94 out of 5 average rating, 17 reviews

NEW* Water View * Heated Pool * near Disney

AndyRating, 5 stars3 weeks ago
From the moment we arrived, we felt completely at home. The space was exactly as described, immaculately clean, beautifully decorated, and full of thoughtful touches that made our stay extra special. The host was incredibly welcoming and responsive, providing clear instructions and always available if and when required. The location was perfect quiet and peaceful, yet close enough to explore everything the area has to offer. Whether we were relaxing indoors or enjoying the nearby attractions, everything about this stay exceeded our expectations. We would absolutely stay here again and highly recommend it to anyone looking for a cozy, comfortable, and memorable Airbnb experience. Thank you for such a wonderful visit!
Guest favorite
An outdoor space showcases a private pool surrounded by a spacious patio. Lounge chairs line the perimeter, and palm trees provide a tropical ambiance. The shimmering water reflects sunlight, while a serene lake is visible in the background, enhancing the tranquil atmosphere.
Home in Four Corners
4.96 out of 5 average rating, 28 reviews

NEW Luxury Reunion Resort Home |Arcades|Theme Room

TiaraRating, 5 stars4 weeks ago
I had a wonderful stay in this home. Everything was beautiful and exactly, if not better, than described. Would definitely stay again! 10 out of 10!
Top guest favorite
A bright, open kitchen features modern white cabinetry and stainless steel appliances. A central island with bar seating complements the space, illuminated by natural light streaming through a skylight. Large windows framed by light curtains enhance the welcoming ambiance.
Home in Kissimmee
4.97 out of 5 average rating, 30 reviews

10 Minutes to Disney - King Bed, BBQ, Pool, Arcade

LucyRating, 5 stars1 week ago
Mike’s place was outstanding and so was the location, We were near Disney and other places. I had a concern and he solved it immediately. The house is very nice. One thing I liked was that we were a party of 10 , with 3 full bathrooms everyone was happy. The play room was perfect for the big and small. We had a very good time and definitely if I should go back to Kissimmee I will stay at Mike’s place. Thank you Mike.

Homes for rent in Kissimmee

Top guest favorite
An inviting pool area glows in soft blue light against the evening sky. The expansive pool features a raised hot tub, surrounded by lounge chairs and palm trees. Lush greenery enhances the serene atmosphere, creating a perfect retreat for relaxation.
Home in Kissimmee
5 out of 5 average rating, 21 reviews

Blissful Pool Villa • Bears Den • 6mi to Disney

LaurenRating, 5 stars3 weeks ago
Absolutely hands down the best rental and hosts I’ve ever experienced. The location was close to everything and great area to walk the pups. The house was very clean and spacious. These hosts go above and beyond to make sure your stay is enjoyable and have everything you need. I will definitely be back when I’m in the area again ⭐️⭐️⭐️⭐️⭐️
Superhost
A round dining table is set with decorative placemats and matching plates, accompanied by silverware and glasses. A centerpiece of greenery adds a natural touch. Modern light fixtures illuminate the space, enhancing the welcoming atmosphere of the dining area.
Home in Kissimmee
4.88 out of 5 average rating, 142 reviews

Stylish 3BR South Heated Pool Just 8 mi to Disney!

MatthewRating, 5 stars4 weeks ago
Great place to stay, the pool is a big plus. The rest of the house is fine, but don’t expect anything special.
Top guest favorite
A single-story home is pictured, featuring a light-colored exterior with brick accents and a neatly maintained front yard. A spacious driveway leads up to a two-car garage. Decorative shrubs line the walkway, while mature trees provide shade in the area.
Home in Kissimmee
5 out of 5 average rating, 10 reviews

Vacation Home from the Vacation 15 min from Disney

CrystalRating, 5 starstoday
Very beautiful Air bnb with a beautiful lake view , Ricardo was an amazing host
Superhost
The outdoor area features a spacious deck with a private pool and spa. A circular table with cushioned chairs is positioned beside the pool. A screen enclosure provides a clear view of the surrounding water and greenery, creating an inviting retreat.
Home in Kissimmee
4.73 out of 5 average rating, 111 reviews

Watersedge of Indian Wells Private Pool & Spa

LukeRating, 5 stars1 month ago
5 stars - 10/10 Excellent location. So close to everything. Busy surrounding roads but we only ever waited one light cycle at nearby crossroads, which is what causes the traffic. A bit of TLC needed. Scuff marks on walls etc but absolutely nothing that will change the quality of your stay / vacation. Great Pool, a few cracks etc but this doesn’t impact the stay at all. Everyone has a solid wood fence around their pools. Therefore not overlooked and good privacy when swimming. The photos don’t do the villa justice. It’s much better. TV’s are all modern flat screens with streaming capabilities. Bedrooms have curtains - not just blinds as shown in the photos. Appliances are immaculate and fully functioning. We had no issues with ants. No issues with cleanliness. It was a peaceful neighbourhood. We would be more than happy to stay here again, and hope we will. Thank you
Guest favorite
A spacious living area features an inviting leather sectional sofa, complemented by a modern coffee table and decorative elements. Natural light fills the space through large windows, highlighting the neutral color palette and sleek cabinetry in the background. The open layout leads to the dining area and staircase.
Home in Kissimmee
4.88 out of 5 average rating, 209 reviews

7BR Stunning Resort by Disney-Private Pool+Hot Tub

ShawnaRating, 5 stars1 week ago
Anne is an outstanding host. Very responsive and her description of the home is spot on! It is a fabulous home that is well appointed and comfortable. Great for families. I would gladly come back. This is truly one of the very best Airbnb’s I have stayed in.
Guest favorite
A screened patio area surrounds a private pool, featuring a unique shape. Comfortable outdoor seating is visible beside the pool, with a backdrop of a two-story home. The vibrant sky transitions from warm tones, creating a serene atmosphere in this outdoor space.
Home in Kissimmee
4.8 out of 5 average rating, 5 reviews

Newly Upgraded 6 Bedroom Dream Near Disney

AshleeRating, 5 stars1 month ago
we had a blast. plenty of space for cheerleaders to get ready in
Top guest favorite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 135 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Rob & LindsayRating, 5 stars1 week ago
A home away from home when visiting Orlando/Kissimmee! The house had plenty of space, it was close in proximity to all of the Orlando attractions, the pool was amazing, and Brian was a top-notch host! Will definitely stay here again!
Top guest favorite
A vibrant game room features eight arcade machines, a pinball machine, and a pool table alongside a cozy couch. Nearby, a private pool area is outlined with colored lights, and themed bedrooms showcase playful decor with bright colors and fun designs. A home theater area presents plush seating on a carpeted floor.
Home in Clermont
5 out of 5 average rating, 13 reviews

Brand New Themed House w Pvt GameRoom&Pool 2159871

ShellRating, 5 stars3 weeks ago
Very nice home. My children enjoyed the theme rooms and pool. We will use them again.

Pet-friendly vacation rentals in Kissimmee

Top guest favorite
The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.
Villa in Kissimmee
4.99 out of 5 average rating, 114 reviews

Beautiful home. Private pool. Close to Disney!

KrisseyRating, 5 stars5 days ago
We had a wonderful stay! Perfect for our family of 7 and our small dogs! Beautiful house and we enjoyed the pool!
Guest favorite
A private pool area is enclosed with a screened structure, featuring a pool with a colorful float. Loungers are placed along the pool's edge, with views of the serene lake and greenery just beyond. The space invites relaxation and enjoyment.
Villa in Kissimmee
4.87 out of 5 average rating, 129 reviews

Villa, Games, Theater, Nr Disney, Great Pool Heat

CarlosRating, 5 stars3 weeks ago
We had a wonderful experience at Paul's residence. We were in 12. We only used 5 of the 6 suites. The kids loved the game room and the movie theater. They played a lot in the pool. The kitchen has an island where we could dine and talk about how the day had been in the Disney parks. The condominium has a prime location, with a Walmart next door and is less than 30 minutes from Disney and Universal Studios. Paul was very careful, always responding to our messages. The house is really a find. The kids loved it and already want to go back. Thank you again, Paul. Greetings from Brazil.
Top guest favorite
A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.
Villa in Kissimmee
4.86 out of 5 average rating, 409 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

NicoletteRating, 5 stars1 week ago
Our stay was fabulous! The house was just as described. Plenty of room for everyone. We enjoyed the pool, used it everyday! We did not end up heating it, which worked out perfect. The temps were so warm during the day and the sun is on the back of the house all day which is great for being out there. The game/movie room was great and kids loved playing and watching movies. Kitchen had what we needed and we cooked all of our dinners there. Fresh crab legs and ahi tuna near by that was great. It is definitely a place we would return to. Thank you so much for sharing your fabulous place for our family to enjoy for the week!!
Top guest favorite
A spacious living area is presented, featuring comfortable black leather seating arranged around a wooden coffee table. Colorful Mickey Mouse artwork adorns the walls, and large glass doors lead to an outdoor space, allowing natural light to fill the room.
Home in Davenport
4.98 out of 5 average rating, 171 reviews

House near Disney-Universal w/pool, game room @EV…

JennyRating, 5 stars1 day ago
Our family had a wonderful stay at Ana’s property. The house was just what we needed for our family of four. The pool was a highlight! Ana was incredibly responsive and we felt right at home. The house is about 20 minutes to Disney and 35 minutes to Universal. My only tiny complaint was that the WiFi was very slow and spotty, but not a huge deal. Otherwise, I would highly recommend this house to anyone traveling to the Orlando area!
Guest favorite
A spacious living area features a light-colored sectional sofa and a round coffee table on a soft rug. The dining area includes a table with seating for six, and the well-equipped kitchen is visible in the background, showcasing modern appliances and bright lighting.
Home in Kissimmee
4.89 out of 5 average rating, 179 reviews

Luxury 8Br/6Ba Villa! ! Resort-Pool-Near Disney

FredaRating, 5 stars3 weeks ago
My group felt right at home staying at Ying's place. He had everything that we needed and more! Lol The house was clean and looks exactly like the pictures. I would be happy to book this home, with Ying being the host, ANYTIME! Ying is an exceptional host!! His communication is TOP TIER! Ying went above and beyond, and made certain accomodations for us when he didn't have too..... THANK YOU YING! 🥹 You are truly a God send. 😁 If you are looking for a nice, spacious house with an incredible host.... look no further.🗣 BOOK THIS HOME!!! Lol ✌🏽
Guest favorite
The private swimming pool is surrounded by a screened enclosure, featuring shimmering blue water. A spa is integrated into the pool design. A safety fence stands nearby, while palm trees and greenery create a serene backdrop. Natural light enhances the inviting pool area.
Home in Davenport
4.83 out of 5 average rating, 230 reviews

Free heated 1st night spa/private pool/min Disney

ModestoRating, 5 stars1 week ago
The place was beyond expectations. Everything was great. Accommodations were extraordinary. I have 0 complaints about this place. I would love to stay there again. I will definitely recommend anyone. As soon as you walk into the house. It smells wonderful, fresh, clean. All the commendations for cooking, we're provided, the swimming pool was clean an inviting. Job, well, done for our host. Thank you so much for letting me stay in your lovely place.
Top guest favorite
An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.
Villa in Kissimmee
4.97 out of 5 average rating, 119 reviews

*Brand New!* Minutes to Disney + Free Resort!

DustinRating, 5 stars1 day ago
The house was very roomy, peaceful and private. They had everything at the house that a family could need! The resort was also a plus with the water park and other amenities. Having a pool right at the house and being so close to Disney were also a HUGE plus! Our entire group loved the house and loved how we weren’t all crowded on top of each other. The grill on site was also a huge plus as we grilled a few nights while we were there. The host is very responsive and answers messages right away! Would definitely recommend to a family traveling to the area and we will more than likely book again! Thank you!
Guest favorite
A vibrant game room is presented featuring colorful lighting and multiple arcade game machines arranged against a stylized wall. The space includes a seating area with a table and chairs, inviting relaxation and play. The playful atmosphere evokes nostalgia for classic video games.
Home in Kissimmee
4.88 out of 5 average rating, 160 reviews

Lakeside Retreat with pool / spa and arcade games

YuriRating, 5 stars1 week ago
Our stay was excellent! The house had all the features as listed. I would definitely consider this property for future family trips. The game room was awesome, and the heated pool and jacuzzi were perfect!

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 740 villa rentals, over 460 condo rentals, over 3,470 house 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

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