Holiday rentals in Kissimmee
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Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,040 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at £8 per night before taxes and fees
Verified guest reviews
Over 277,640 verified reviews to help you choose
Family-friendly holiday rentals
5,830 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,120 rentals that welcome pets
Holiday rentals with a pool
6,330 properties feature pools
Rentals with dedicated workspaces
3,970 properties have a dedicated workspace
Wifi availability
6,950 of Kissimmee holiday rentals include wifi 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 holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
Epic stay at Vista Cay!
This 2-bedroom, 2-bathroom apartment at Vista Cay Resort, Orlando, offers an exceptional location for enjoying the best of the city. Just minutes from Orlando International Airport and Walt Disney World, it provides unparalleled convenience for both travelers and residents. Additionally, its proximity to the Convention Center, Universal Studios, SeaWorld, and International Drive grants easy access to major attractions, dining, and shopping, offering a complete experience in the heart of Orlando.
FamilyLocationSleep quality
4.95 out of 5 average rating, 61 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!
ValueLocationQuiet
4.96 out of 5 average rating, 176 reviews
*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!
FamilyLocationParks
4.92 out of 5 average rating, 215 reviews
12BR Disney Luxury Retreat - Pool, Theater & Fun!
Welcome to our magical vacation home in Orlando, just minutes from Universal Studios, located on International Dr, less than 2 miles from SeaWorld! Featuring 12 themed bedrooms inspired by beloved movies like Harry Potter, Frozen, and Aladdin, and a Tiana-themed kitchen, every detail is designed to delight guests of all ages. With 21 beds, it’s perfect for families and groups. Enjoy a prime location, unique decor, and ultimate comfort for an unforgettable stay. All themed environments.
LocationValueBathroom
4.98 out of 5 average rating, 58 reviews
Villa Resort Club
Welcome to Villa Resort Club! Lovely 4-bed/2.5-bath for 8 with screened private pool and games room. Fully equipped kitchen, workspace, washing machine/tumble dryer, parking, and WiFi. Pet-friendly. Minutes from Disney. A quiet, comfortable home base! Welcome to Villa Resort Club! House with 4 bedrooms and 2.5 bathrooms for 8, screened pool and games room. Fully equipped kitchen, workspace, washer/dryer, parking, Wi-Fi. Pets welcome. Minutes from Disney. Quiet and comfortable!
FamilyLocationGetting around
4.88 out of 5 average rating, 179 reviews
Luxe Family Escape | Pool Oasis Near Disney
Welcome to your Luxe Family Escape near Disney! ✨ Located in one of Kissimmee’s exclusive golf communities, this home offers the perfect mix of relaxation and fun. Enjoy your private screened pool, hammock, ping pong, and charming backyard gazebo. Inside, you’ll find stylish bedrooms, a fully equipped kitchen, and comfortable living spaces. The perfect private oasis for families and groups looking to enjoy Disney, Orlando’s attractions, and a relaxing Florida getaway. 🌴🏊
LocationHospitality
5.0 out of 5 average rating, 4 reviews
4BR Disney & Universal Themed Villa Reunion Resort
Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.
LocationFamilyGetting around
5.0 out of 5 average rating, 23 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!
FamilyLocationBathroom
4.96 out of 5 average rating, 119 reviews
12BR Disney Beach house 34 ppl Pool Theater Arcade
Stay near Walt Disney World in this luxury 12-bedroom Orlando vacation home, perfect for large families and groups. Enjoy a private pool and hot tub, movie theater, Transformers game room, poker table, outdoor kitchen, and themed Minions, Moana, Scooby-Doo, Inside Out, and Lilo & Stitch bedrooms. With multiple king suites and space to relax, play, and reconnect, it’s the perfect Disney-area getaway for reunions and unforgettable group vacations.
FamilyLocationBathroom
4.97 out of 5 average rating, 101 reviews
Disney's Pool House
Magical family retreat in Central Florida! Just minutes from Disney, this spacious home features fun Disney-themed decor, a private screened pool, game room with pool table and air hockey, smart TVs, full kitchen, free Wi-Fi, and washer/dryer. Close to Universal, SeaWorld, CityWalk, and International Drive—perfect for families looking to relax, explore, and create unforgettable memories in the heart of all the action!
FamilyValueAccess
4.82 out of 5 average rating, 60 reviews
Luxury Reunion Retreat Patio Views Near Disney
Located in the desirable Spectrum Condo at Reunion Resort, this comfortable 5‑bedroom, 4‑bathroom condo offers a relaxing and convenient home base for families and groups looking to explore all that Orlando has to offer. With a well‑designed layout and comfortable furnishings, this condo provides the perfect balance of privacy and togetherness, making it an ideal choice for your next getaway.
LocationCheck-inHospitality
5.0 out of 5 average rating, 3 reviews
Brand new luxury near clubhouse / lake view (405)
STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! Modern Lake View Apartment – Near Disney, Universal , Outlets This beautiful apartment was fully redecorated with all-new furniture by B & Design (By Barbara Costa), featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake.
LocationFamilyDecor
4.9 out of 5 average rating, 21 reviewsPopular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
12BR | 11.5 BA > Sports Game Room!
LocationFamilyParking
4.82 out of 5 average rating, 90 reviews
Haunted Mansion-inspired Ghoulish Sanctuary
LocationFamilyPool
4.98 out of 5 average rating, 40 reviews
*Modern Condo Resort/Pool/Spa/15 Min to Disney*
LocationValueGetting around
4.98 out of 5 average rating, 42 reviews
Orlando Dream Escape | Private Pool | Disney
LocationFamilyAccuracy
4.83 out of 5 average rating, 18 reviews
Amazing Home Near Parks w/ Pool & Spa
LocationValueCheckout
5.0 out of 5 average rating, 9 reviews
12 Bd/ 11.5 Ba Sleeps 24! Veranda Palms (2444 RD)
LocationValueBathroom
4.76 out of 5 average rating, 41 reviews
6 miles from Disney ! Private pool ! 4 bedrooms
FamilyLocationComfort
4.88 out of 5 average rating, 8 reviews
Disney/Universal Villa w/ Pool
LocationValueWalkability
4.91 out of 5 average rating, 74 reviewsWhen is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £113 | £117 | £125 | £128 | £109 | £113 | £111 | £97 | £89 | £94 | £106 | £125 |
| 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
Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.
What are the top things to do in Kissimmee?
Old Town
Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.
Fan Boat Swamp Tour
Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.
Hot Air Balloon Ride
Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.
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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
- Camping World Stadium
- Kia Center
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- LEGOLAND Florida Resort
- Old Town
- ChampionsGate Golf Club
- ICON Park
- Disney's Hollywood Studios
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure