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Vacation rentals in Kissimmee

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Kissimmee

  • Total vacation rentals

    Explore 7,040 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at G$2,090 GYD per night before taxes and fees

  • Verified guest reviews

    Over 277,640 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,830 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,120 rentals that welcome pets

  • Vacation rentals with a pool

    6,330 properties feature pools

  • Rentals with dedicated workspaces

    3,970 properties have a dedicated workspace

  • Wi-Fi availability

    6,950 of Kissimmee vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Lake access across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Top-rated vacation rentals in Kissimmee

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

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Guest favorite
A Star Wars-themed game room is featured, complete with multiple screens displaying iconic scenes. An air hockey table and foosball setup are visible, alongside gaming chairs arranged for comfortable seating. The room is brightly lit, emphasizing the vibrant decor that adds to the entertainment atmosphere.
Villa in Kissimmee
4.96 out of 5 average rating, 208 reviews

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

Make memories to last a lifetime in our luxurious 9-bedroom home (sleeps 24) at Orlando's premier vacation community. Enjoy your own Star Wars game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and just a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

Top guest favorite
Home in Davenport
4.91 out of 5 average rating, 169 reviews

Magical Pool Villa-close to Disney Game/movie Room

The magic starts the moment you walk through the door—and the memories will last a lifetime! ✨ Our themed vacation home features Mickey Mouse, Toy Story, Frozen, Star Wars and Minion rooms with motion-activated songs, UV artwork, and LED lighting. Enjoy a private pool with color-changing lights, BBQ area, sun loungers, and a fun-filled game room with air hockey and arcade games. Designed to delight kids and adults alike with immersive sights, sounds, and magical details throughout the home!

Guest favorite
A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.
Villa in Kissimmee
4.93 out of 5 average rating, 114 reviews

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

Superhost
A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.
Home in Buenaventura Lakes
4.91 out of 5 average rating, 156 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Guest favorite
Home in Kissimmee
4.9 out of 5 average rating, 10 reviews

Orlando Dream Escape | Piscina Privada | Disney

Disfruta de esta hermosa casa renovada con piscina privada en Kissimmee. Ideal para familias y grupos de hasta 8 huéspedes. Cuenta con 3 habitaciones, 2 baños, sofá cama, cocina totalmente equipada, Wi-Fi, lavadora, secadora y estacionamiento gratuito. Ubicada cerca de Disney, Universal, SeaWorld, restaurantes y tiendas. Relájate, disfruta del sol y crea recuerdos inolvidables con familia y amigos. ¡A solo minutos de las principales atracciones de Orlando ✅ Piscina privada

Top guest favorite
A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.
Home in Kissimmee
4.98 out of 5 average rating, 104 reviews

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

Guest favorite
Home in Kissimmee
4.93 out of 5 average rating, 27 reviews

New! Eights Mansion Themed House w/pool by Disney

Enjoy soft opening rates!! Unbeatable location minutes from Disney Parks and Restaurant Row! This guarded, gated home is perfect for family trips and sleeps up to 16 guests. Enjoy a Stunning Christmas 12-ft tree, 8 bedrooms , themed rooms including Mickey, Princess, Cabin, StarWars, Moana, and Mario, 2 Master bedrooms and a large private movie theater for unforgettable nights. Perfect for families seeking comfort, fun, & holiday magic close to the parks year-round

Top guest favorite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport
4.95 out of 5 average rating, 108 reviews

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

Guest favorite
A galaxy-themed home theater is equipped with reclining leather chairs and plush bean bag seating. Colorful LED lighting creates an immersive ambiance, while a large screen displays a scene of a tropical beach. The walls are adorned with painted stars and planets.
Home in Davenport
4.94 out of 5 average rating, 67 reviews

7 BR Galactic Favorite Davenport

Relax and un-wind in our beautiful seven bedroom family-friendly resort inspired vacation home, just 15 minutes away from Disney World. Our spacious fully-furnished two-storey home is perfect for family getaways or gatherings with friends. Enjoy preparing your dinner in your fully equipped kitchen with high-end appliances and dining alfresco by your private pool and hot tub or get cozy in the galaxy-inspired theatre for a family movie night!

Top guest favorite
A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.
Home in Kissimmee
4.98 out of 5 average rating, 121 reviews

Lakefront Villa w/pool 4mi to Walt Disney World

"Private South-Facing Pool (Sun All Day!)" and "Peaceful Lakefront Views with Local Wildlife "are just some of our guest's comments. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Guest favorite
Home in Kissimmee
4.88 out of 5 average rating, 8 reviews

7851 Luxury 5BR Home w/ Private Pool Near Disney

Create unforgettable memories in this modern 5-bedroom, 5-bathroom home in Reunion Village, near Disney. Enjoy a private screened-in pool, game room, second-floor loft, open-concept living and dining area, modern kitchen, multiple king-sized bedrooms, themed bedrooms, high-speed Wi-Fi, TVs, washer/dryer, free parking, self check-in, and access to eligible Encore Club amenities. Ideal for families and groups.

Guest favorite
A private cinema room features plush reclining seats arranged for viewing a large screen. Blue and purple lights create a vibrant atmosphere, while a bar area with stools is visible in the background. The screen displays a scenic landscape, enhancing the entertainment experience.
Home in Kissimmee
4.9 out of 5 average rating, 48 reviews

No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!

**We offer a FREE EV Charger! We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.

Popular amenities for Kissimmee vacation rentals

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,134 GYDG$32,388 GYDG$34,477 GYDG$30,716 GYDG$27,164 GYDG$28,835 GYDG$30,507 GYDG$26,746 GYDG$24,656 GYDG$25,910 GYDG$29,253 GYDG$34,477 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Kissimmee?

    Kissimmee has accommodations in resort areas near theme parks, private homes around Reunion and Storey Lake, and family-friendly neighborhoods with easy access to local attractions. Many spaces feature pools, spacious layouts, and outdoor amenities for group stays.

  • What are the best things to do in Kissimmee with kids?

    Families can explore fun attractions like Gatorland, ride thrilling coasters at Old Town, or enjoy large playgrounds and splash pads in city parks. Themed entertainment and interactive experiences are frequently suggested for younger visitors.

  • What are some of the best things to do in Kissimmee?

    Discover live shows and rides at Old Town, visit Gatorland for wildlife encounters, or explore regional history at the Osceola County Historical Society. The area is also known for airboat tours and vibrant outdoor markets.

  • How is the weather in Kissimmee?

    Kissimmee has mild winters around 49–72°F (10–22°C) and hot, humid summers reaching 74–92°F (23–33°C) with frequent rainfall from May through September. Lightweight clothing, sunscreen, and a rain jacket are recommended.

  • What are the best places to visit in Kissimmee?

    Popular places include Old Town for entertainment and shops, Gatorland for reptile encounters, and the Kissimmee Lakefront Park with walking trails and playgrounds. Museum enthusiasts will often find exhibits at local historical centers.

  • What are some hiking trails in Kissimmee?

    Stroll boardwalks and shaded paths at Shingle Creek Regional Park, walk lakeside trails at Kissimmee Lakefront Park, or explore nature preserves nearby. Trails often highlight local wildlife and peaceful scenery.

  • What are some family activities we can do in Kissimmee?

    Explore Gatorland’s exhibits, ride classic attractions at Old Town, or play in the splash pads at Kissimmee Lakefront Park. Family-friendly dining spots and arcades are also popular choices for shared outings.

  • What are some of the best day trip ideas from Kissimmee?

    Explore Orlando’s theme parks, stroll nature reserves around Lake Tohopekaliga, or enjoy coastal beaches for a change of scenery. You can also visit nearby state parks or experience local wildlife tours.

  • Are there any pet friendly accommodations available in Kissimmee?

    Many Kissimmee neighborhoods, including those near Central Kissimmee and the resort communities, have pet-friendly vacation rentals. Parks and outdoor spaces throughout the area make traveling with pets convenient.

  • What are some local tips for visiting Kissimmee?

    Hydrate frequently in warm months, and bring insect repellent for outdoor activities near lakes. Book popular attractions in advance and explore local eateries for regional flavors beyond the main tourist areas.

  • What is Kissimmee known for?

    Kissimmee is known for its proximity to major theme parks, distinctive wildlife experiences like Gatorland, and vibrant entertainment districts such as Old Town. Airboat rides and access to lakes add an outdoor adventure element.

  • What are the best hidden gems to explore in Kissimmee?

    Visit Shingle Creek Regional Park for quiet paddling and wildlife spotting, shop local at farmers markets, or discover history at the Osceola County Historical Society museum. Neighborhood spots often have authentic flavors and art.

  • What are the best foods to try in Kissimmee?

    Enjoy Southern-style barbecue, fresh seafood, and Latin flavors like Cuban sandwiches or empanadas at locally rooted eateries. Homemade ice cream and citrus-inspired desserts are frequently suggested, especially in summer.

  • What should I bring for a trip to Kissimmee?

    Pack lightweight clothing, sunscreen, and a hat for sun protection. A rain jacket, comfortable walking shoes, and insect repellent are useful for exploring parks and outdoor attractions.

  • What is the nightlife in Kissimmee like?

    Kissimmee has lively spots for live music, themed bars, and outdoor events in areas like Old Town. Nighttime entertainment often includes family-friendly shows and locally owned restaurants with late-night menus.

  • What are the most popular events or festivals in Kissimmee?

    Kissimmee hosts car shows, holiday parades, and cultural festivals around Old Town, with seasonal fairs and outdoor concerts often taking place in parks. Late spring and holiday weekends feature many community gatherings.

  • Are there family friendly vacation rentals in Kissimmee?

    Family-friendly vacation rentals are available throughout Kissimmee, particularly in resort-style neighborhoods and private home communities. Many have amenities like pools, recreation rooms, and easy access to parks and attractions.

  • When is the best time to visit Kissimmee?

    Late autumn and early spring are often recommended, with milder temperatures and smaller crowds. Summer brings lively local events and frequent afternoon rain, while winter stays mild and sunny.

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.

What are the 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee