Vacation rentals in Kissimmee
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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$2,092 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.
*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15
JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!
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!
Sleeps 20✦Free Pool Heat✦15 min to Disney✦Hot Tub
Make memories to last a lifetime in our luxurious 9-bedroom home (sleeps 20) at Orlando's premier vacation community. Enjoy your own Marvel game room, private pool (heated at no extra charge*), and hot tub. Our 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 3-minute walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!
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.
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!
Orlando Dream Escape | Private Pool | Disney
Enjoy this beautiful renovated house with a private pool in Kissimmee. Ideal for families and groups of up to 8 guests. It has 3 bedrooms, 2 bathrooms, a sofa bed, a fully equipped kitchen, Wi-Fi, a washer, a dryer and free parking. Located near Disney, Universal, SeaWorld, restaurants, and stores. Relax, enjoy the sun, and create unforgettable memories with family and friends. Just minutes from Orlando's top attractions! ✅ Private pool
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!
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.
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.
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.
2026 Themed NEW 08 Bedrooms At Solara Resort
Our vacation homes will bring you to experience beyond a simple stay. You will be near the most famous themed parks in the world while feeling the comfort of your home, plus having the highest standard of luxury and modernity, with everything a vacation home in Orlando can offer you.
Cozy family home w/ heated pool 15 min. to Disney
Modern family home in a gated community (very quiet neighborhood). 2391 sq ft with 5 bedrooms, 4.5 bathrooms, heated pool*, BBQ*, gaming room, 60'' Full HD TV, free unlimited high-speed wi-fi, central AC/Heating. 15 minutes driving to Disney.
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
9 Themed Bedrooms, Pool & Jurassic Theater
Private Pool + Spa | Game Room | Near Disney
4BR Disney & Universal Themed Villa Reunion Resort
Brand New 12br/33 ppl-Pool/Arcade/Theatre
New! Epic Dream House with Pool
5 Bd/ 3.5 Ba Sleeps 16! Cumbrian Lakes (4645 CL)
VillaLumine•PrvtPool•Heater•Aesthetic•NearDisney
Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool
Kissimmee beach vacation rentals
STar Island 1 Bedroom
Comfy Studio w/ private Entrance
Family Friendly w/ KING bed, Resort Pool Sleeps 5
PentHouse Suite with 2X View
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Water Front Haven
Exclusive 8BR Themed Villa • Private Pool Retreat
Beach Resort with pool tiki bar near Disney World
Family friendly vacation rentals in Kissimmee
Disney Retreat| Heated Pool & Game Room| Champions
Themed Disney Villa | Pool | Arcade | Resort ºoº
Rotating VR Machine, Arcade, Slide | 3mi to Disney
Themed Villa:10 min to Disney: Pool, Gameroom, BBQ
No Airbnb Fees! Home Pool/ Game Room/Resort 288881
Luxury Home sleeps 28 - Games, Swimming, theatre
RU Incredible Parents? Themed-7bed, 4mi. to Disney
Magical Family Fun House Near Disney Luxury Villa
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,167 GYD | G$32,422 GYD | G$34,514 GYD | G$30,749 GYD | G$27,193 GYD | G$28,866 GYD | G$30,539 GYD | G$26,774 GYD | G$24,683 GYD | G$25,938 GYD | G$29,284 GYD | G$34,514 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°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.
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Old Town
- Tinker Field
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- LEGOLAND Florida Resort
- ICON Park
- ChampionsGate Golf Club
- Aquatica