Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Casa Bella Mediterranean Style near Disney
Welcome to this beautifully 4-bedroom, 3-bath pool home located in the desirable Westside Tuscany community — a peaceful Mediterranean-style enclave just minutes from Walt Disney World and Orlando’s world-class attractions. Step inside to a bright and spacious open living area with large windows and sliding doors that lead directly to your private screened pool, where you can relax and enjoy peaceful wooded views after a fun day at the parks. Enjoy your own private Florida retreat! Book now!
3 bedroom Villa in Kissimmee
The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.
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.
2697 Resort 4BR House Waterpark by Disney Orlando
Minutes from Disney, stylish & peaceful Townhouse, with 4 bedrooms and 3 full bathrooms, fully equipped kitchen for up to 8 guests, located in the family friendly Storey Lake Resort. Enjoy our private pool with optional water heater. The open floor plan blends Kitchen, Dining and Living room. Close to outlet malls & retail stores. Great Resort amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Lake, Kayak, Tiki Bar, Ice Cream Shop & more.
Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!
Family Vacay with Pool near WDW!
We hope to welcome you to this enchanting family retreat in Kissimmee, Florida, just 20 minutes from the magic of Walt Disney World Resort! This sunlit oasis is designed for unforgettable family vacations. Dive into your screened private pool, a cool oasis under the warm Florida sun, to create memories that'll last a lifetime. After an exhilarating day at the parks, return to this cozy home where you'll find the perfect blend of entertainment and relaxation.
Waterfront Wizarding Near Universal's Harry Potter
This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.
Luxury Home w/ Pool & 6 Beds near Disney
Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.
Pet-Friendly Pool Home Near Orlando
Welcome to your perfect Orlando retreat! This beautiful and spacious home offers a blend of modern comfort, stylish design, and exceptional amenities — all just minutes from the top parks and attractions. Enjoy a private screened-in pool, elegant interiors, and thoughtfully designed spaces ideal for families, groups, or long stays. Every detail has been curated to provide comfort, relaxation, and an unforgettable vacation experience.
Storey Lake brand new near Disney lake & club view
STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! This beautiful apartment was fully redecorated with all-new furniture by B & Design, featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake. Located in a luxury resort just minutes from Disney parks, Universal Studios, outlets, Walmart, Publix, and the airport.
COZY Villa w/ Private Pool & Game Room | Kissimmee
Welcome to this cozy and modern townhome located in Kissimmee, near Disney. The perfect choice for those looking for peace of mind, offering themed rooms, private pool, game room, and modern decoration. • Community: Le Reve • 4 Bedrooms/ 3.5 Bathrooms/ Sleeps 10 • Disney (7.1 mi) SeaWorld (10.7 mi) Legoland (32.8 mi) • Convention Center (10.1 mi) Universal Studios (14.1 mi) • Location: Le Reve Court, Kissimmee, FL 34746
Disney/Orlando Animal Kingdom Luxy Stay
Our Animal Kingdom themed house is located only short 15 amay from Disney Parks. Includes 4 themed bedrooms, heated pool, fully stuffed kitchen and relaxing spa for mom. Arcade, board games form entire family, and Poker table for older kids.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Luxury 4BR Villa Golf View /Theater/Huge Pool&Spa
Solara9120 Drift| 6BR Villa w/ Pool & Luxury Spa
Jewel of Emerald Island with Heated Pool!
Dreamy 5 Bed w/ Game Room, Pool & Themed Bedrooms!
*Modern condo on resort. No fees 15-Min to Disney*
The Eights House by Disney. Themed Island Dream
4BR/3BA Townhouse w/ Private Pool in Storey Lake
Large Private Home on Golf course by Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £111 | £115 | £123 | £109 | £97 | £103 | £109 | £95 | £88 | £92 | £104 | £123 |
| 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.
Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,260 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at £15 per night before taxes and fees
Verified guest reviews
Over 267,190 verified reviews to help you choose
Family-friendly holiday rentals
5,840 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,160 rentals that welcome pets
Holiday rentals with a pool
6,460 properties feature pools
Rentals with dedicated workspaces
4,030 properties have a dedicated workspace
Wifi availability
7,170 of Kissimmee holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Pet-friendly and Laptop-friendly workspace across Kissimmee rentals
4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club