Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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PentHouse Suite with 2X View
Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!
Luxury 5BR free heat private pool Disney Universal
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!
Neverland Found-Minutes from Disney Free Waterpark
Welcome to Neverland Found! This unique property inspires us to never grow up with themed rooms of Peter Pan, The Lost Boys, and Tinkerbell. Our home has 2 Master Suites, a fully equipped kitchen, 5 bedrooms, 5 baths, pool and spa, Pirates of the Caribbean game room, and loft area. Our home is located in the resort community of Storey Lake with access to multiple clubhouses and pools and all of it's amenities. Located within minutes of the theme parks & attractions that Orlando has to offer.
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.
-A Sweet Home Near Theme Parks!-
Step into your ultimate vacation escape! This residence is perfectly positioned to offer easy access to all the best attractions and hotspots in the Kissimmee/Orlando region. Enjoy the convenience of having major theme parks such as Disney, Universal, Seaworld, ICON, and even airports, all within a short 20-25 minute drive. Nestled on a corner lot, this home boasts abundant parking, a spacious yard, and plenty of amenities, ensuring you feel right at home from the moment you arrive!
15 minutes from Disney Luxury Retreat at Reunion
Relax after a magical day at Disney or Universal. Welcome to Reunion Luxury Retreat, experience the perfect blend of luxury comfort, and privacy in this elegant villa, located within the exclusive gate community of Reunion Village, just minutes from Orlando's world-famous theme parks. Our Home offers everything you need for an unforgettable stay. 4 spacious bedrooms, 5 different pools in our resort. Gate community with 24-7 security. Fast wifi , smart TV, fully equipped kitchen.
Modern Condo with Lake View Near Disney 3151
STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!
1BD Cottage "Limoncello" in Margaritaville
Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)
5BR Golf View Penthouse • Near Disney • Luxe Stay!
✨ Spacious 5BR Loft Condo near Disney! ✨ Located in a gated resort, this stylish family-friendly getaway features a full kitchen, washer/dryer, and access to a resort pool, fitness center, and game room. Just minutes from Walt Disney World, Universal, and shopping outlets. Sleeps 12—perfect for large families or group trips. Enjoy comfort, space, and unbeatable location for your Orlando vacation! Book your dream stay now! 🏰🌴💫
Home 6 BDR at Solara Resort/Private Pool LED
The Space * Accommodates: 16 * Bedrooms: 6 * Bathrooms: 4.5 * Property type: Luxury Villa * Location: Solara Resort * ONLY 0.2 miles away from The Clubhouse! * 12 miles from Magic Kingdom * 8 miles from Animal Kingdom * 16 miles from SeaWorld * 21 miles from Universal Studios * Property and resort close to the US 27 highway where some restaurants, market, gas station, pharmacies are located.
*EPIC Bunk Slide*Minutes to Disney*FREE Pool Heat*
In a Galaxy far far away… You and your band of rebels will journey to a small rebel outpost, in the coveted Windsor Hills Resort, to find your way with the force. Located just 5 miles from Walt Disney World Resort and 20 minutes from Universal Orlando and SeaWorld! Follow us on Insta @galactic_escape_kissimmee
Shells Cottage 12 miles from Epic Universe
This Shell themed one bedroom one bathroom cottage is fully equipped for your stay. From the upgraded kitchen appliances and floors, to the comfortable queen sized bed and comfortable sitting room, this cottage is perfect for honeymooners, vacationers and business travelers!
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
Spacious Cozy 5-Bedroom house
Family Getaway w/ Pool & Arcade – Near All Parks !
Sweet vacation home.
The Villa Stay
Welcome to the Oasis near Disney!
New! Epic Solara Playhouse | Custom Bunks + Slides
Solara Villa with Themed Rooms and Private Pool
Home away from Home
Kissimmee beach vacation rentals
STar Island 1 Bedroom
Comfy Studio w/ private Entrance
Family Friendly w/ KING bed, Resort Pool Sleeps 4
Perfect Disney\Golf Vacation
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Your Family's Disney HQ~Sleeps 8~No Extra Fees!
Water Front Haven
Beach Resort with pool tiki bar near Disney World
Family friendly vacation rentals in Kissimmee
Storey Lake 5BR Villa w. Pool&Spa & Water Park
Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub
Magical Hideaway - 15 min to Disney - Storey Lake
Disney Themed home with Private Pool & Lazy River!
Disney Orlando vacation home with private pool 3
Winter Sale*Free Pool Heat/WaterPark/Parkings
Magical Pool Villa-close to Disney Game/movie Room
Game & Theater Room, Castle Bunks, Pool & Spa
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$29,458 GYD | G$30,293 GYD | G$31,547 GYD | G$30,711 GYD | G$27,160 GYD | G$28,831 GYD | G$30,502 GYD | G$26,742 GYD | G$24,652 GYD | G$25,906 GYD | G$29,249 GYD | G$34,472 GYD |
| 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
Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.
Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.
What are the top things to do in Kissimmee?
Kissimmee Lakefront Park
The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.
Museum of Military History
Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.
Twin Oaks Conservation Area
The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.
Quick stats about vacation rentals in Kissimmee
Total vacation rentals
Explore 7,330 vacation rentals in Kissimmee
Nightly prices starting at
Kissimmee vacation rentals start at G$4,178 GYD per night before taxes and fees
Verified guest reviews
Over 262,660 verified reviews to help you choose
Family-friendly vacation rentals
6,190 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 1,210 rentals that welcome pets
Vacation rentals with a pool
6,620 properties feature pools
Rentals with dedicated workspaces
4,060 properties have a dedicated workspace
Wi-Fi availability
7,280 of Kissimmee vacation rentals include wi-fi 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
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Give Kids the World Village
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club