Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291
Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!
Waterfront next to Resort by Disney Game &Theater
Lakefront Luxury Everything is Completely remodeled 5 bdrms\5 bthrms luxury villa – Located in the gated Paradise Palms Resort,which is just around the corner from Disney. Only a few steps away from the Clubhouse amenities & nature path,this home offers privacy & lake\nature views from the sun soaked south facing color changing pool\spa.Enjoy , New home theater, two 1st floor master bdrms & 2 bthrms + another master & immersive themed rooms on 2nd floor. AC Arcade TV gameroom & billiards Loft
8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.
Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!
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.
Dream Vacation | Sleeps 18 | Themed Arcade & Rooms
Experience the magic of Disney World, Universal Studios, and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in Storey Lake Resort, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, Universal Studios, Sea World, Premium Outlet Malls, and beyond! This modern property is focused on providing an unforgettable and exceptional family centric vacation experience!
"Paradise Found" Sensational 6 Bed Home W/Peloton
Discover 'Paradise Found' at Windsor at Westside, a 6-bed fantasy home near Disney. This 3,300 sq ft gem offers an open-plan living space, gourmet kitchen, and a private pool oasis with a BBQ, dining and lounge. Enjoy a king suite with pool access, a fun-filled garage gym/games area, and a vast upstairs lounge with Xbox. Dream in themed children's rooms or one of the three king bedrooms. Perfect for families seeking a magical retreat! Free resort access, pool heat and BBQ.
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 you’ll enjoy a resort-style pool, jacuzzi, splash area, lazy river, and more. Comfort, fun, and convenience all in one place!
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!
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!
Jacuzzi Magic Village 4 suites near Disney & 192
MAGIC VILLAGE VIEWS - 8 GUESTS - 4 SUITES - BBQ - JACUZZI - 06 MIN DISNEY Magic Village Views, new condominium, with houses of modern contemporary architecture, rooms with double height ceilings, contemporary furniture, terrace with barbecue and parking spaces in front of the unit. Well located near US-192, 6 minutes from Disney parks, 25 minutes from Universal, 26 minutes from Sea World, 3 minutes from pharmacies and Walmart. (3081 Rcf way)
"Casa Kiwi" Margaritaville Cottage 5 min to Disney
Enjoy your own private hot tub in this standalone cottage located inside Margaritaville resort. Located off 192 in Kissimmee 5-10 minutes to Disney parks and 20-30 minutes to Universal Studios and Seaworld. The Promenade at Sunset walk which is inside the resort (walking distance from cottage) has over a dozen restaurants that cover every type of cuisine you can think of
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
Magical 6BR at Encore Resort next to Disney - 453
Luxury Townhouse Near Disney | 3BR
Family Vacay with Pool near WDW!
Guest Home_ Orlando Airport and Disney
Modern Condo: 10 Min to Disney + Fireworks Views!
9BD - Storey Lake - Newly Themed - Theatre, Games
6BR Oasis w/ Private Pool, Game Room & Lanai
Newly Built Villa with Pool, Cinema & Games Room
Kissimmee beach vacation rentals
STar Island 1 Bedroom
Comfy Studio w/ private Entrance
Perfect Disney\Golf Vacation
PentHouse Suite with 2X View
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Charming Villa near Disney, pool, 3 beds, sleeps 5
Cozy Condo 15 minutes away from Walt Disney
Beach Resort with pool tiki bar near Disney World
Family friendly vacation rentals in Kissimmee
Fully themed, free arcade, south facing pool & spa
Magical Luxury Townhouse/CG Resort/Close to Disney
Magical Pool Villa-close to Disney Game/movie Room
New! Eights Mansion Themed House w/pool by Disney
Brand New 9 Bedrooms Single Family Solara 87SA
5 Themed Rooms+GameRoom&Pool+Windsor Island Resort
Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool
4BR/3BA Townhouse w/ Private Pool in Storey Lake
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,171 GYD | G$32,426 GYD | G$34,518 GYD | G$30,753 GYD | G$27,196 GYD | G$28,870 GYD | G$30,543 GYD | G$26,778 GYD | G$24,686 GYD | G$25,941 GYD | G$29,288 GYD | G$34,518 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$4,184 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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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Camping World Stadium
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- University of Central Florida
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports