Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Gorgeous 5BR PetFriendly @Encore Near Disney 7693
Modern, stylish, and luxurious, 3000sf home, with 5 bedrooms, at the world's renowned Encore Resort at Reunion. It features a game room, a huge backyard, an oversized private pool, spa. A true dream vacation home. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE
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!!
Private Pool & Free Heat - Close to Disney!
3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms
Magical 5-Bedroom Villa Near Universal's Wizarding
Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.
Kissimmee cottage *15mi to WDW*
Brand new private home in Mill Creek RV park. 1 bedroom home with queen bed and additional pull out sofa. Play yard/crib available for 5th guest. Full kitchen, washer/dryer in home. Enjoy a central location backing onto a green space with pond for peaceful privacy on the back deck. Full access to all Mill creek amenities ( pool, gym, playground, corn hole, pickle ball, putting green) 2 smart TV’s in unit 1 mile to Walmart 15 mile to Disney World & Universal 13 mile to Orlando airport
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.
Magical Stays Near Disney
✨🏰 Magical Disney Escape 🏰✨ Stunning 4BR/3BA home with 2 kings, 1 queen, 2 twins & huge L-shaped couch! 🌟 Splash in your private pool, relax on the lanai, or battle in the Star Wars glow-in-the-dark game room 🎮. Enjoy board games, movies, and smart TVs with Netflix/HBO/Amazon 📺. Newly renovated kitchen & in-house washer/dryer 🧺. Minutes from Animal Kingdom, Disney Springs & all parks — perfect for families & groups! 🎢✨ Free WiFi, parking, and all the magic you need!
Twist of Lime Cottage in Margaritaville nr Disney
Welcome to your own island-inspired oasis. Our charming cottage "Twist of Lime" 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.
Cozy House with Private Pool. Kissimmee/Orlando
Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.
"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool
🏡 Welcome to Disney Serenity, your Orlando villa near Disney with a private heated pool, game room, and home theater. Enjoy resort perks like a lazy river, gym, and tiki bar. Located minutes from Disney World and Universal, this wheelchair‑friendly retreat blends comfort, accessibility, and family‑ready fun.
Small World Cottage, 12 miles from Epic Universe
Is there a more charming, family friendly resort in the Disney area? Walking distance to Old Town and Fun spot, minutes to Disney, this resort has all the amenities you could need. All are welcome!
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
Private Pool Home Near Disney | 4BR Sleeps 10
Charming King Suite, Near Universal & Pet-Friendly
Kissimmee
Stylish & Clean Home Free ResortAccess 2364
Near Disney/Private Pool/Steps to Resort Amenities
6BR Oasis w/ Private Pool, Game Room & Lanai
Haunted Mansion-inspired Ghoulish Sanctuary
Sophisticated 4 En Suites w/ Private Hot Tub & BB
Kissimmee beach vacation rentals
STar Island 1 Bedroom
Comfy Studio w/ private Entrance
Family Friendly w/ KING bed, Resort Pool Sleeps 5
Perfect Disney\Golf Vacation
PentHouse Suite with 2X View
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Water Front Haven
Cozy Condo 15 minutes away from Walt Disney
Family friendly vacation rentals in Kissimmee
4BRThemed/Pool/Near Disney/PetsOk/Free BBQ&Resort
No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291
Magical Moments Luxury Disney Villa, Pool & Arcade
Magical Disney House-Pool & Hot Tub,Free Waterpark
6BR Disney Villa | Pool, Spa & Theater | Sleeps 14
Your Dream Vacation—Disney Magic Brought to You!
Disney-Themed & Arcade Rooms • Summerville Resort
New! Epic Dream House with Pool
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,179 GYD | G$32,434 GYD | G$34,527 GYD | G$30,760 GYD | G$27,203 GYD | G$28,877 GYD | G$30,551 GYD | G$26,784 GYD | G$24,692 GYD | G$25,947 GYD | G$29,296 GYD | G$34,527 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 7,260 vacation rentals in Kissimmee
Nightly prices starting at
Kissimmee vacation rentals start at G$4,185 GYD per night before taxes and fees
Verified guest reviews
Over 267,190 verified reviews to help you choose
Family-friendly vacation rentals
5,840 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 1,160 rentals that welcome pets
Vacation rentals with a pool
6,460 properties feature pools
Rentals with dedicated workspaces
4,030 properties have a dedicated workspace
Wi-Fi availability
7,170 of Kissimmee vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Beachfront, and Lake access 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field