Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Margaritaville Cottage 10 Minutes to DisneyWorld!
āØ Location, Location, Location! Weāre conveniently located in the beautiful Margaritaville Resortājust a short drive from all the Orlando fun: š¢ Disney World š¬ Universal Studios š SeaWorld š“ Sunset Walk š¦ H2O Water Park ā ļø Please Note: This stay does not include access to resort amenities or the main pool. However, many guests choose to purchase access to H2O Water Park using the savings from resort fees! āø» š Nearby Highlights š½ļø Sunset Walk A vibrant destination filled with restaurants, shopping, live entertainment, and a movie theater. š¦ H2O Water Park Located right on the resort property with fun for all ages. Additional fees apply. š· Formosa Garden Winery Just a 5-minute walk! Enjoy wine, beer, and beautiful views. Open ThursdayāSunday ā we highly recommend making a brunch reservation! āø» š” Cottage Accommodations ā¢ 2 spacious bedrooms ā¢ 2 full bathrooms ā¢ Convertible couch (turns into a queen bed) ā¢ Free & easy parking ā¢ Free WiFi ā¢ TVs with cable in the living room + both bedrooms (Netflix & Disney+ included) ā¢ High ceilings ā¢ Back patio with lounge chairs ā¢ Second-floor balcony with two Adirondack chairs ā¢ Fully stocked kitchen ā¢ Gated security + 24-hour watch āø» š House Rules š« No parties under any circumstance (per Airbnb policy) š No smoking ā $200 fine if violated š„ No unregistered guests š¾ Pets If you plan to bring a pet, please let us know before arrival. ā¢ $50 service fee ā¢ Max 2 pets
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
Tahiti Gilās Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to FarĆ© 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 āstory dwellingā adventure from the moment you step thru the door! - Kungaloosh!!
Feel the Magic 9 min Disney, Pool & Pet friendly
āØ Looking for comfort, privacy, and fun near Disney? Our home features a private pool and spa, perfect for relaxing after the parks. Optional pool heating is available for $49 per night. Thoughtfully prepared for families, the house welcomes guests, including those traveling with pets, for easy Florida days. Magic Kings House invites you to create unforgettable moments at Windsor Palms, a favorite resort among guests. Every detail has been carefully arranged to provide a memorable stay.
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.
Waterfront Condo minutes to Disney & Universal
Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlandoās top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.
Cozy Orlando Area Cottage - 4 Miles to Disney
With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.
*Modern Luxury Reunion Oasis | Pool, Spa & Cinema
Wow-factor luxury meets unforgettable family fun, just minutes to Disney, at this show-stopping home in the exclusive Reunion Resort. Step outside to a massive 2,400-sq-ft southwest-facing pool deck with outdoor kitchen, private pool, overflow spa, and no rear neighborsāperfect for all-day sun and sunset swims. Inside: private movie theater, billiards game room, and spectacular Star Wars & Frozen II theme bedrooms with tube slide, plus Xbox and PlayStation for nonstop entertainment.
Sanctuary w/ Game Room + Pool | Walk to Clubhouse
Welcome to an unforgettable Orlando getaway! This fabulous 6-bedroom villa in Windsor at Westside is just minutes from Disney and top attractions. Perfect for families and large groups, it features a private east-facing pool with Bbq grill, fun themed bedrooms, and a game room for all ages. Only a 6-minute walk to the clubhouse, where youāll enjoy a resort-style pool, jacuzzi, splash area, lazy river, and more. Comfort, fun, and convenience all in one place!
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.
9 bdrm heated pool, Free water park EV charger
Our huge stunning luxury villa with private heated pool & spa situated in the gated resort of Windsor at Westside, appx -15 minutes from Disney. ā¢ Up to 20 people can enjoy their dream vacation in our 9 Bedroom, 6 Bath villa ā¢ lovely Lake view from the private Pool ā¢ Free access to waterpark, 5 min walk. ā¢ 2 car driveway, 1 car garage with EV charging, free street parking. ā¢ address: Gobi drive, Kissimmee, 34747
Quiet Room Close to Disney and Attractions
Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
7 BR Galactic Favorite Davenport
Lovely Themed Villa w/ Private Pool | Storey Lake
Brand New 12br/33 ppl-Pool/Arcade/Theatre
355 Luxury House | Patio | GameRoom | Pool | Grill
Modern Luxury Kissimmee Retreat
7839 6BD Beautiful Family Home in Reunion Resort
Luxury 5BR Villa with Private Pool + Water Park
Haunted Mansion-inspired Ghoulish Sanctuary
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
PentHouse Suite with 2X View
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Water Front Haven
Exclusive 8BR Themed Villa ā¢ Private Pool Retreat
Family friendly vacation rentals in Kissimmee
Themed Disney Villa | Pool | Arcade | Resort ĀŗoĀŗ
Super Mario's Sky Suite - Epic Universe 3 BD SUITE
Mickey Fantasia Family Friendly w/accessibility
Disney Escape 4Br w/Resort Access-Storey Lake
4m Disney Sun, Free Snacks, Golf, Poolā¢ Spaā¢ Games
Brand New - 10br - Sleeps 26 - Theatre/Arcade/Pool
Disney StarWars home 20 min to Disnay World dw3
Water Slides & luxury resort minutes from Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,174 GYD | G$32,429 GYD | G$34,521 GYD | G$30,755 GYD | G$27,198 GYD | G$28,872 GYD | G$30,546 GYD | G$26,780 GYD | G$24,688 GYD | G$25,943 GYD | G$29,291 GYD | G$34,521 GYD |
| Avg. temp | 16Ā°C | 18Ā°C | 20Ā°C | 22Ā°C | 25Ā°C | 27Ā°C | 28Ā°C | 28Ā°C | 27Ā°C | 24Ā°C | 20Ā°C | 17Ā°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 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.
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$4,184Ā 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 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
- 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