Vacation rentals in Kissimmee
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Quick stats about vacation rentals in Kissimmee
Total vacation rentals
Explore 7,040 vacation rentals in Kissimmee
Nightly prices starting at
Kissimmee vacation rentals start at $10 per night before taxes and fees
Verified guest reviews
Over 277,640 verified reviews to help you choose
Family-friendly vacation rentals
5,830 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 1,120 rentals that welcome pets
Vacation rentals with a pool
6,330 properties feature pools
Rentals with dedicated workspaces
3,970 properties have a dedicated workspace
Wi-Fi availability
6,950 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
Top-rated vacation rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness, and more.
Pool Spa + Outdoor Entertainment | Golf Retreat
Escape to a one-of-a-kind golf retreat in Davenport, where resort-style outdoor living meets family-friendly entertainment. Spend your days relaxing by the private pool & spa, enjoying movies on the outdoor TV, and challenging the family in the Super Mario game room, all just minutes from Disney Whether you're planning a family vacation, golf getaway, or long weekend with friends, this beautifully renovated 4-bedroom home was designed for connection, comfort, and unforgettable Florida memories.
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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 overflow 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.
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Luxury Retreat at Reunion Resort
Luxury Retreat at Reunion Resort ā 12 Miles from Disney! Welcome to our stunning vacation home nestled in the prestigious Reunion Resort! This elegant getaway offers the perfect blend of luxury, comfort, and convenience, making it an ideal retreat for families and groups. The home offers a beautiful back yard pool and spa area for you to enjoy, while playing music through the surround sound system in the house and in the back yard. EV Friendly. With 6 Bedrooms You wont regret staying here.
LocationFamilyIndoor spaces
Villa Resort Club
VILLA LUJOSA - BARRIO SĆPER HERMOSO POOL HEATER HOUSE - DiviĆ©rtete con toda la familia en este alojamiento con estilo moderno , te encantarĆ” el Ć”rea de picnic frente de la casa , el Ć”rea de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niƱos y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARĆ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.
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7490 Magic Village 8 guests 4,5 baths 8 min Disney
MAGIC VILLAGE VIEWS - 8 GUESTS - 4 SUITES - 4,5 BATHS - BBQ - 8 MIN DISNEY Excellent, secure gated community with just 192 homes featuring contemporary architecture. It boasts great security and parking available right in front of each home. Located in a prime area near US-192. Nearby, you'll find movie theaters, restaurants, water parks, and shopping centers. It is just 8 minutes from Disney parks. Additionally, it is only 3 minutes away from pharmacies and Walmart. (7490 Brl dr)
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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.
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10 Min to Disney | Kings | Heated Pool | Games
āØ Perfect family getaway just minutes from Disney magic! āØ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. š° Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!
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Orlando Dream Escape | Piscina Privada | Disney
Welcome to your perfect Orlando getaway! Enjoy this beautifully renovated home with a private pool, just 20 minutes from Disney, Universal, and SeaWorld. Perfect for families and groups of up to 8 guests. Features 3 bedrooms, 2 full bathrooms, a fully equipped kitchen, fast Wi-Fi, washer & dryer, free parking, and self check-in. Relax, unwind, and create unforgettable memories close to Orlandoās best attractions, shopping, and restaurants. šāāļø Private Pool
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Royal Retreat Disney Themed Pool Home, Arcade, Theater
Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!
ValueFamilyWifi
Montego Bay Retreat | 15 Min to Disney
Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlandoās top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! āØ
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Luxe Family Retreat | Pool Villa Near Disney & MCO
Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlandoās top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.
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No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!
**We offer a FREE EV Charger! We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.
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Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
Luxury Lakefront Villa ā¢ Pool, Hot Tub, Game Room!
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4BR Disney & Universal Themed Villa Reunion Resort
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Star Wars & Wizard Themed XL Pool Home Near Disney
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2026 New Themed 06 Bedrooms at Solara Resort
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5 Bd/ 3.5 Ba Sleeps 16! Cumbrian Lakes (4645 CL)
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VillaLumineā¢PrvtPoolā¢Heaterā¢Aestheticā¢NearDisney
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Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool
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Large Private Home on Golf course by Disney
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Kissimmee beach vacation rentals
Comfy Studio w/ private Entrance
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Perfect Disney\Golf Vacation
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Family Friendly w/ KING bed, Resort Pool Sleeps 4
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PentHouse Suite with 2X View
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Luxury Waterfront | 1 Mile to Disney | Sleeps 7
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Water Front Haven
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Exclusive 8BR Themed Villa ā¢ Private Pool Retreat
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Waterfront/KayakFishing/nearDisney&LakeTohoa/Pets
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Family friendly vacation rentals in Kissimmee
Luxury 9BR Disney Home|FREE H Pool & Solara Resort
ValueFamilyPool
9 Themed Bedrooms, Pool & Jurassic Theater
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Magical Disney Family Escape with Pool & Game Room
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Themed Disney Villa | Pool | Arcade | Resort ĀŗoĀŗ
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Pool | Themes | Game Room
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5 BD/ 5.5 BA Sleeps 14! Windsor Cay (15847 CC)
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Dazzling 9 BR+Brand New MARIO KART @ Champion Gate
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New Themed home w/pool in Margaritaville Poco Loco
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When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 | $155 | $165 | $169 | $144 | $149 | $146 | $128 | $118 | $124 | $140 | $165 |
| Avg. temp | 61Ā°F | 64Ā°F | 67Ā°F | 72Ā°F | 77Ā°F | 81Ā°F | 83Ā°F | 83Ā°F | 81Ā°F | 75Ā°F | 68Ā°F | 63Ā°F |
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 49ā72Ā°F (10ā22Ā°C) and hot, humid summers reaching 74ā92Ā°F (23ā33Ā°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 Gatorlandās 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 Orlandoās 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 Floridaās 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 Kissimmeeās 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 parkās 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 Kissimmeeās 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 Americaās 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 Floriaās native wildlife habitats. Tall, untamed grass pokes through the parkās 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 parkās main, elevated viewing platform, where you may be able to spot one of Floridaās most well-recognized reptiles, the alligator, or even a bald eagle.
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- SeaWorld Orlando
- Disney Springs
- Universal Orlando Resort
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Aquatica
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