Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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BestValue by Disney*SouthFace Pool&Spa*Theater
Start your unforgettable vacation in this beautiful 7 Bed 5.5 Bath Disney themed home located in Orlando's Luxury Vacation Resort Windsor Island. This modernly furnished two-story home features South Facing Heatable Private Pool/Spa, Game Room, Home Theater with 120'' Projection Screen, Themed Bedrooms with Bunk beds, Multiple Gathering Areas and and Downstairs Master Suite! You'd also enjoy all the awesome resort amenities FOR FREE- including Lazy River, Mini Golf, Arcades, Pickleball & Gym
8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
A vacation home that takes your entertainment seriously! Thatās our 8-bedroom villa in Emerald Island Resort at 3 miles from Disneyā¦ 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! Weāre 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 everyoneās 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.
"Magical 8BR Resort Oasis: Pool, Themes & Games!"
Welcome to Grand Orlando! Discover a luxurious 8-bedroom retreat at Windsor at Westside Resort, featuring a grand open-plan living space, a fully-equipped kitchen, and two large dining tables. Enjoy a Marvel-themed game room, a Pixar loft with a giant movie screen, and themed bedrooms including Star Wars and Harry Potter. Outdoors, find a LED-lit pool with color-changing lights, a BBQ area, and an outdoor TV. The perfect blend of comfort and magic for an unforgettable stay.
Modern 4bdr Storey Lake w/themed rooms near disney
Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.
House by the Mouse: Something for Everyone!
Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!
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!
The Real Florida Whispering Oaks
The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!
Retreat w/ Pvt Pool + Club Access | Disney 15min
Experience comfort, style, and resort living in this beautiful 5-bedroom, 5.5-bathroom vacation home just 15 minutes from Disney. Enjoy elegant living spaces, Smart TVs throughout the home, an Xbox One, and a private screened pool area with patio furniture and a BBQ grill ā perfect for relaxing after a fun day in Orlando. The open-concept kitchen and spacious dining area are ideal for gathering with family and friends.
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 youāre here to relax or explore, this home offers everything you need for an unforgettable stay.
There is no other place you want to be than here.
āØ Experience Orlando in style! This 4BR, 3,100 sq. ft. retreat is just 10 min from Disney. Enjoy your own private pool, hot tub, and full sun all day in a quiet upscale community. Bright open living, chefās kitchen, and spa-inspired relaxation make it the perfect escape after the parks. Pets welcome at no extra charge. Close to shops, dining, and attractionsābook your luxury getaway today!
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
Luxory/Championsgate/private Pool/2 gulf courses
Themed Rooms, Pool, Theater & Arcade | Sleeps 22
contemporary home w/ private pool, near parks
Modern King Apt w Water view, Pool Gym Near Parks
Charming vacation villa on resort w/private pool
Disney Orlando vacation home with private pool 4
NBA Dream Mansion | 15BR Luxury Villa w/ Pool
Kissimmee
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
Lakefront home - country - check for seasonal rate
Luxury Waterfront | 1 Mile to Disney | Sleeps 7
Water Front Haven
Beach Resort with pool tiki bar near Disney World
Family friendly vacation rentals in Kissimmee
Magical Hideaway - 15 min to Disney - Storey Lake
Magical Moments Luxury Disney Villa, Pool & Arcade
4BR Disney & Universal Themed Villa Reunion Resort
Themed Disney Villa | Pool | Arcade | Resort ĀŗoĀŗ
Dazzling 9 BR+Brand New MARIO KART @ Champion Gate
Your Dream VacationāDisney Magic Brought to You!
Dream Vacation | Sleeps 18 | Themed Arcade & Rooms
DisneyTheme Storey Lake Resort Pool/Spa/BBQ6Br/5b
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ļŗ©.ļŗ547 | ļŗ©.ļŗ569 | ļŗ©.ļŗ606 | ļŗ©.ļŗ540 | ļŗ©.ļŗ477 | ļŗ©.ļŗ507 | ļŗ©.ļŗ536 | ļŗ©.ļŗ470 | ļŗ©.ļŗ433 | ļŗ©.ļŗ455 | ļŗ©.ļŗ514 | ļŗ©.ļŗ606 |
| 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 ļŗ©.ļŗ73 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
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- 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
- University of Central Florida
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club