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.
Casita bonita
You'll love this unique and romantic escape of our tiny home — perfect for couples or solo travelers seeking a peaceful retreat. Nestled in a quiet neighborhood, this space features everything you need: a comfy full size bed, a compact but fully equipped kitchen, and a relaxing outdoor area. Enjoy morning coffee on the back patio, stargazing at the stars and the simplicity of tiny living with modern comforts. Just minutes from local attractions, Disney, Epic universe, Sea World, Volcano Bay, etc
3191-307 Resort Lake View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!
Private Suite with Independent Entrance
Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!
Perfect Getaway. Private Pool.Kissimmee/Orlando
This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.
Disney Escape 4Br w/Resort Access-Storey Lake
Welcome to your dream getaway in Kissimmee! This cozy 8-guest home in Storey Lake Resort – The Cove invites you to relax and enjoy every moment. Take a dip in your private heated pool (no extra cost), fire up the BBQ grill, or have fun with the Nintendo Switch. Kids will love the two themed bedrooms;Star Wars and Frozen! TVs offering full streaming access with multiple apps. You’ll also have access to two resort clubs with pools, lazy river, slides, gym, and tiki bar — everything you need !
Small Studio Apartment
The apartment is attatched to the main house, but has its own entrance. The studio will provide guest with complete privacy The kitchen is equipped with a fully furnished setup; including pots, pan oven, fridge and more. Full size bed is provided. Bathroom will have towels, soap, shampoo, conditioner, and hair dryer Othe amenities include a TV with Netflix, wifi, Alexa, window AC unit, parking right in front, and a quiet neighborhood. Any questions or concerns you can contact me.
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!
Orlando Private Tiny Guest House
*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know
Luxury Encore Pool Spa Pets Game Rm Theater Gym
Amazing Brand New Modern Luxurious Home at Encore Resort @ Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much Much More Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **
"Independent Golden Suite" Near the Disney Parks
✨"Golden Suite" in Kissimmee✨ Your perfect getaway near Disney's attractions! Welcome to a cozy modern family-friendly suite designed for up to 4 guests. Enjoy two full-size beds, a fully equipped kitchen and dining area, private entrance, and dedicated guest parking Just minutes away from Disney World, Universal Studios, Aquatica and more. After a fun-filled day, return home where you can relax with your loved ones. 🌟Book now and experience the magic of Kissimmee🌟
The Tuxedo 2BR • Pool • Near Disney & Old Town
Black & White Modern 2BR Getaway. Welcome to The Tuxedo, where modern style meets comfort. This bold 2 bedroom, 2 bathroom ground-floor apartment offers more than just a place to sleep. It’s a clean, thoughtfully designed space for travelers who value simplicity, convenience, and location. Just 25 minutes from Old Town and a short drive to Disney and Universal, it's the perfect base for your Florida stay, whether you're here for work, play, or a little of bot!
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.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
(#4.Tripoli) Relaxing bed-Kissimmee. Disney.
Rm#2: Cozy Modern Room – weekly & Monthly Discount
ROOM#1 Coral Cay Resort Welcome Disney
9. Small room in paradise Resort+ FREE waterpark
Private Bathroom & Close Airport,Park & Everything
Clean and comfy King bedroom
2 mi 2 outlets! Near Disney! Room in shared home
Magical Room 13 min from Disney and Outlets
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $182 SGD | $188 SGD | $195 SGD | $190 SGD | $168 SGD | $179 SGD | $189 SGD | $166 SGD | $153 SGD | $163 SGD | $175 SGD | $206 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 7,290 holiday rentals in Kissimmee
Verified guest reviews
Over 257,530 verified reviews to help you choose
Family-friendly holiday rentals
6,160 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,150 rentals that welcome pets
Holiday rentals with a pool
6,590 properties feature pools
Rentals with dedicated workspaces
4,000 properties have a dedicated workspace
Wifi availability
7,110 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
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Rentals with a washing machine and dryer Kissimmee
- Cabin rentals Kissimmee
- Rentals with a cinema Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with an EV charger Kissimmee
- Beachfront rentals Kissimmee
- Private suite rentals Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Guest house rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with pools Kissimmee
- Villa rentals Kissimmee
- Rentals with breakfast Kissimmee
- Cottage rentals Kissimmee
- Family-friendly rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Beach house rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Holiday home rentals Kissimmee
- Apartment rentals Kissimmee
- Waterfront rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with lake access Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Mansion rentals Kissimmee
- Hotel rooms Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with a hot tub Kissimmee
- Flat rentals Kissimmee
- Rentals with a kayak Kissimmee
- Tiny house rentals Kissimmee
- House rentals Kissimmee
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Shingle Creek Golf Club