Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!
Vacation Home 3 bedroom/2 full bath/private pool
Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**
Cozy Condo Only 6 Minutes From Disney World
Step into our inviting condo, where coziness embraces you! Our charming property is strategically located only 6 minutes from the Theme Parks, prestigious Outlets, and excellent Restaurants. Experience the comfort of having ample space for up to 5 guests, with a King Size bed in the suite and a Twin-Full Bunk Bed available. Experience luxury living with our high-quality furniture and decor. Our Condo is fully equipped with a modern open-style kitchen and appliances, high-speed WiFi 5G, Cable
Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!
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 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.
Luxury Townhouse Near Disney | 3BR
Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!
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.
The Eights House by Disney. Themed Island Dream
Location can't get better! Next to Disney Parks and Restaurant Row! This Guarded and gated place to stay is perfect for family trips. You will fall in love with our year round 12ft tree tastefully decorated by season. Mickey's Camping room, Frozen themed room, the cabin Christmas year round experience & 2 additional modern king rooms perfect for couples! Did I mention the stunning Avengers Home theater/game room and oversized pool?
Modern Vacation Home Near Disney SL4962
✨ Welcome to your dream vacation home! This modern 4-bedroom townhouse comfortably hosts up to 12 guests and features a private splash pool. Located near Disney, shopping, and dining, it’s perfect for families and groups. Enjoy a fully equipped kitchen, TVs in every bedroom, washer & dryer, and access to resort amenities including pools, lazy river, gym, and splash park. Self check-in included!
8052 Heated Pool Grill House Kissimmee by Disney
Relax with the whole family at this peaceful HEATED POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 4 Smart TV's and strong Wi-Fi all around the house. Enjoy our Games Room with a Foosball table and a Pool table located in the garage!
Casa Resort Storey Lake a minutos de Disney y Epic
Espectacular casa en Storey Lake Resort, con 4 habitaciones para 12 personas y piscina privada. Perfecta para familias que buscan comodidad y diversión. Acceso a río lento, piscinas, toboganes, mini-golf y gimnasio. A solo 10–15 min de Disney, 20–25 min de Universal y 15–20 min de SeaWorld. Ubicación ideal para unas vacaciones inolvidables.
2026 NEW Brand NEW 07 Bedrooms At Solara Resort
* Accommodates: 18 * Bedrooms: 07 * Bathrooms: 06 * Property type: Single Family * Location: Solara Resort - This is a new property located in the PHASE 3 of the Solara Resort. -The club house is located on PHASE 1 of the same resort.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
207 Storey Lake Brand new 7 Guests 2 BDR Lake view
Family Vacay with Pool near WDW!
Wheelchair Accessible Home | ADA Bath + Pool Lift
2362 SW 6BD - Amazing Sunny Pool - Near Disney
NEW Modern Townhome w/ Themed Room | Near Disney
Luxury 4 Bedroom Home - Resort Access! Disney!
Romantic getaway. Cabin w/ Indoor Soaking Tub
Windsor Palms Villa with Very Private Pool
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £105 | £108 | £113 | £110 | £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 7,330 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at £15 per night before taxes and fees
Verified guest reviews
Over 262,660 verified reviews to help you choose
Family-friendly holiday rentals
6,190 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,210 rentals that welcome pets
Holiday rentals with a pool
6,620 properties feature pools
Rentals with dedicated workspaces
4,060 properties have a dedicated workspace
Wifi availability
7,280 of Kissimmee holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Gym 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
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Give Kids the World Village
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Shingle Creek Golf Club
- Universal's Islands of Adventure