Holiday rentals in Kissimmee
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
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!
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.
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.
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!
Top1% *La Piu Belle* Retreat at Storey Lake View
Welcome to **La Piu Belle Retreat** – a stylish, sunny, and serene escape at Storey Lake Resort. This 2-bedroom condo features boho-chic decor, a fully equipped kitchen, a bright balcony, and cozy vibes throughout. Enjoy access to a water park, gym, and more. Perfectly located just minutes from Disney, premium outlets, and top restaurants. Excellent Reviews: Our guests rave about their experiences, highlighting our cleanliness, location, and exceptional service.
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.
Jacuzzi Magic Village 4 suites near Disney & 192
MAGIC VILLAGE VIEWS - 8 GUESTS - 4 SUITES - BBQ - JACUZZI - 06 MIN DISNEY Magic Village Views, new condominium, with houses of modern contemporary architecture, rooms with double height ceilings, contemporary furniture, terrace with barbecue and parking spaces in front of the unit. Well located near US-192, 6 minutes from Disney parks, 25 minutes from Universal, 26 minutes from Sea World, 3 minutes from pharmacies and Walmart. (3081 Rcf way)
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.
Retreat w/ Pvt Pool + Club Access | Disney 15min
Experience comfort, style, and resort living in this beautiful 5-bedroom, 5.5-bathroom vacation home just 15 minutes from Disney. Enjoy elegant living spaces, Smart TVs throughout the home, an Xbox One, and a private screened pool area with patio furniture and a BBQ grill — perfect for relaxing after a fun day in Orlando. The open-concept kitchen and spacious dining area are ideal for gathering with family and friends.
Modern Rock Star Suite
Located at the gates of Walt Disney World, this modern Rockstar Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Restaurants, Shopping and many more. Wonderful lake / pool view with sunrise. Enjoy!
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
Lovely Themed Villa w/ Private Pool | Storey Lake
Fantasy World, The Lego Villa, Free Waterpark
Gorgeous 4BDRM Fully Furnished minutes from Disney
5565Torino
Modern & Bright • Near Disney & Outlets
3 Bed Pool/Spa w/ Sunset Water in Margaritaville
Disney Getaway, Hot Tub, 10 min to Parks, 6 people
7839 6BD Beautiful Family Home in Reunion Resort
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $190 SGD | $197 SGD | $210 SGD | $187 SGD | $165 SGD | $176 SGD | $186 SGD | $163 SGD | $150 SGD | $158 SGD | $178 SGD | $210 SGD |
| 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.
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 $25 SGD 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, Beachfront and Gym across Kissimmee rentals
4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Hotel rooms Kissimmee
- Rentals with breakfast Kissimmee
- Guest house rentals Kissimmee
- Waterfront rentals Kissimmee
- Beach house rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with a fireplace Kissimmee
- Private suite rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Villa rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- House rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Family-friendly rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a cinema Kissimmee
- Beachfront rentals Kissimmee
- Rentals with lake access Kissimmee
- Holiday home rentals Kissimmee
- Flat rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with beach access Kissimmee
- Mansion rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Serviced apartment rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Cabin rentals Kissimmee
- 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
- Magic Kingdom Park
- Orlando / Kissimmee KOA
- 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!
- Southern Dunes Golf and Country Club
- University of Central Florida
- ChampionsGate Golf Club