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$2,092 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.
150 Inch 4K Movie Theater Pool & Spa sleeps 16
"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.
4.83 out of 5 average rating, 320 reviews
Disney 5BR • Private Pool Free Heat • Pet Friendly
Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!
4.96 out of 5 average rating, 176 reviews
Encanto at Emerald Island-Pool House by Disney
POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!
4.9 out of 5 average rating, 126 reviews
10 Minutes to Disney | Heated Pool, Arcade, Kings
🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!
4.99 out of 5 average rating, 159 reviews
Sunny-All-Day Pool Vacation Home
Welcome to our Sunny 3-Bedroom Retreat! This inviting home features 3 spacious bedrooms, a south-facing pool for all-day sun, and a private fenced yard. Enjoy the bright living space, modern kitchen, and outdoor oasis with comfortable seating. Conveniently located near local attractions, dining, and shopping. Additional amenities include high-speed Wi-Fi, smart TV, air conditioning, washer and dryer, and free parking. Book now for a perfect getaway! **No parties ($500 fine) and no smoking**
4.94 out of 5 average rating, 107 reviews
The Lakeview Oasis - XL Pool & Jacuzzi - Orlando
Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!
4.96 out of 5 average rating, 144 reviews
6 miles from Disney ! Private pool
This Beautiful newly renovated 3 bedroom 2.5 bathroom luxury townhouse has a private pool with complimentary resort facilities. The house is close to the Resort and Clubhouse, which has a lobby/reception, snack bar, all-year heated pools, training facilities, and a game room. It is 15 minutes from all Disney parks and close to Orlando attractions. Orlando International Airport is just 40 minutes from the home. Very relaxing and cozy. Newly renovated with new appliances and furniture.
4.85 out of 5 average rating, 321 reviews
Haunted Mansion-inspired Ghoulish Sanctuary
Welcome, Foolish Mortals... To the Ghoulish Sanctuary: An immersive Haunted Mansion-themed stay just 15 minutes from Walt Disney World, where candlelights flicker, and the air is deathly still... Experience a one-of-a-kind Haunted Mansion-themed stay for up to 6 people. This spooky rental in Kissimmee lets you inhabit your favorite ghostly estate... if you dare. Ready to play your next campaign and need a place to gather for your DnD weekend? The sanctuary and its spirits await.
4.98 out of 5 average rating, 40 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!
4.96 out of 5 average rating, 118 reviews
Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney
Welcome to this modern 12-bedroom, 11.5-bath home—perfect for your next family getaway! Comfortably sleeping up to 32 guests, this centrally located retreat is just 15 minutes from the Disney parks. Enjoy fantastic amenities including a private pool and spa, a home theater for movie nights, and a fun-filled game room. With plenty of space and entertainment for all ages, it’s the ideal spot for family reunions, group vacations, and special get togethers.
4.86 out of 5 average rating, 100 reviews
Near Disney • 4BR • Perfect for Families
Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!
4.97 out of 5 average rating, 266 reviews
Private Heated Pool & BBQ Included Near Disney
Stay close to Orlando’s top attractions in this modern 4-bedroom, 3.5-bath vacation home for up to 10 guests. Enjoy your own private heated pool and built-in BBQ, both included with your stay, plus a bright open living area, full kitchen, fast Wi-Fi, laundry, and family-friendly sleeping spaces. This home is a great fit for families, extended families, and groups who want more space, privacy, and comfort than multiple hotel rooms.
4.89 out of 5 average rating, 157 reviewsPopular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
6BR Home w/ Priv Pool Near Disney Gated Resort
4.93 out of 5 average rating, 14 reviews
2026 Themed NEW 08 Bedrooms At Solara Resort
4.87 out of 5 average rating, 15 reviews
Disney's Pool House
4.82 out of 5 average rating, 60 reviews
NEW 2026 Themed 9BR| Racing Simulator |Solara
4.75 out of 5 average rating, 4 reviews
12BR Disney Luxury Retreat - Pool, Theater & Fun!
4.98 out of 5 average rating, 58 reviews
Epic stay at Vista Cay!
4.95 out of 5 average rating, 60 reviews
Orlando Dream Escape | Piscina Privada | Disney
4.82 out of 5 average rating, 17 reviews
12BR | 11.5 BA > Sports Game Room!
4.82 out of 5 average rating, 90 reviewsKissimmee beach vacation rentals
PentHouse Suite with 2X View
4.96 out of 5 average rating, 203 reviews
Luxury PH Direct Disney Fireworks View from Apt
4.9 out of 5 average rating, 102 reviews
Comfy Studio w/ private Entrance
4.95 out of 5 average rating, 131 reviews
Water Front Haven
4.93 out of 5 average rating, 28 reviews
1st level Pool/Beach Disney Area
4.98 out of 5 average rating, 60 reviews
Family Friendly w/ KING bed Sleeps 4 midterm avail
4.82 out of 5 average rating, 108 reviews
Exclusive 8BR Themed Villa • Private Pool Retreat
4.76 out of 5 average rating, 33 reviews
UniqueStay w Lakeview/DisneyFireworks/WaterSports
4.9 out of 5 average rating, 10 reviewsFamily friendly vacation rentals in Kissimmee
Super Mario's Sky Suite - Epic Universe 3 BD SUITE
4.95 out of 5 average rating, 194 reviews
5BR Disney Pool Villa | Arcade + Spa | Sleeps 11
4.95 out of 5 average rating, 120 reviews
OMG! Disney Area, Movie Theater, Game Room & Pool!
4.87 out of 5 average rating, 457 reviews
Magical Pool Villa-close to Disney Game/movie Room
4.9 out of 5 average rating, 177 reviews
Cozy family home w/ heated pool 15 min. to Disney
4.9 out of 5 average rating, 211 reviews
Free Waterpark, Fantasy World, The Mickey House
4.83 out of 5 average rating, 137 reviews
Themed Disney Villa | Pool | Arcade | Resort ºoº
5.0 out of 5 average rating, 143 reviews
6BR Family Fun Starts Here with Pool & Games 4354!
4.88 out of 5 average rating, 141 reviewsWhen is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,177 GYD | G$32,432 GYD | G$34,524 GYD | G$35,361 GYD | G$30,130 GYD | G$31,177 GYD | G$30,549 GYD | G$26,783 GYD | G$24,690 GYD | G$25,946 GYD | G$29,293 GYD | G$34,524 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
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Epcot
- Universal's Volcano Bay
- Kia Center
- Camping World Stadium
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Old Town
- LEGOLAND Florida Resort
- ChampionsGate Golf Club
- ICON Park
- Disney's Hollywood Studios
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure