Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!
Stylish Condo 20 mins to Disney/King Bed
Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!
Villa Resort Club
VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.
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.
2BD Cottage w/Spa in Margaritaville
Welcome to your own island-inspired oasis. Our charming 2Bd spa cottage 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. Relax with the whole family at this peaceful place to stay.
Tranquil Azure Haven 10 Min to Parks Pets Friendly
Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY
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 Eights House by Disney. Themed Island Dream
Location can't get better! Next to Disney Parks and Restaurant Row! This Guarded and gated place to stay is perfect for family trips. You will fall in love with our year round 12ft tree tastefully decorated by season. Mickey's Camping room, Frozen themed room, the cabin Christmas year round experience & 2 additional modern king rooms perfect for couples! Did I mention the stunning Avengers Home theater/game room and oversized pool?
The Villa Stay
Welcome to a stunning retreat perfectly located near Orlando’s top attractions, world-famous theme parks, delicious restaurants, and premier shopping destinations are all just moments away. After an exciting day exploring the city, come home to a space designed for relaxation and style. Unwind in modern comfort, enjoy peaceful surroundings, and make unforgettable memories in this elegant villa.
Comfy Home with Hot Tub at Kissimmee/Orlando area
✨ Stylish and family-friendly retreat in a great Kissimmee location! Enjoy a comfy stay with a relaxing hot tub for up to 6 people and a fully equipped kitchen, perfect for creating meals together. Designed for comfort and convenience, ideal for your Orlando and Kissimmee vacation. IMPORTANT INFORMATION: 🚫 Parties or events are not allowed on the property or surrounding area. 🚭 No smoking.
Bright Modern Townhome Retreat
Step into modern comfort at this brand new 3 bedroom, 3 bath townhome in The HUB at Westside Reserve. With bright open living spaces, stylish finishes, and thoughtfully laid out bedrooms, this home offers a relaxing retreat just minutes from Disney, Winter Garden, and local essentials. Whether you’re here for fun or convenience, this home delivers in comfort and location.
Private pool - gatted community
Welcome to this comfortable 4-bedroom home located at Encore Condominium, Southfield Street, Kissimmee, FL. This property offers privacy, spacious common areas, and excellent proximity to Orlando’s top attractions. Please note that guests do not have access to any Encore Resort amenities.
Popular amenities for Kissimmee vacation rentals
Other great vacation rentals in Kissimmee
Lake View Heated Pool Home 3BR&2BT 10’ to Disney.
Decadent Penguin - Storey Lake by Shine Villas
Solara9120 Drift| 6BR Villa w/ Pool & Luxury Spa
Modern & Bright • Near Disney & Outlets
10BR Theater Pool Little Mermaid Alice 16295
Brand New Luxury 4BDRM home near Disney
WorldMark Reunion Three Bedroom
Special Offer Storey Lake Free Waterpark WS4352
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $195 CAD | $201 CAD | $209 CAD | $204 CAD | $180 CAD | $191 CAD | $202 CAD | $177 CAD | $163 CAD | $172 CAD | $194 CAD | $228 CAD |
| 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
Located in central Florida, Kissimmee is well situated near some of the most sought-after attractions in the state. Being so close to the Walt Disney World Resort, Universal Orlando Resort, and LEGOLAND Florida parks ensures that this city is popular with families and theme-park fans alike. Kissimmee has its own set of charms to entice visitors, including easy access to the Florida Everglades, the Kennedy Space Center, and many aquatic attractions. You can spend jam-packed days enjoying the company of fairy-tale creatures and riding thrill rides, then change it up with visits to the natural world and dreams of reaching for the stars in outer space. The city has its share of nationally known dining options to cater to visitors from around the world, including entertainment districts that combine the best in food, shopping, and fun. Whether you’re looking for magical lands, family fun, or a wide variety of entertainment options, Kissimmee will deliver an unforgettable holiday experience.
What are the top things to do in Kissimmee?
Immerse Yourself in Magical Worlds
Kissimmee is minutes from some of the most popular theme parks in the world. From exploring the four Walt Disney World Resort parks to channeling wizarding magic and superhero power at Universal Orlando Resort and building vacation memories at LEGOLAND Florida, central Florida’s theme parks are not to be missed.
Kennedy Space Center Visitor Complex
Defy gravity and reach for the stars at this gateway to space exploration. The center features behind-the-scenes tours of launch sites and spaceflight facilities, a walk-through rocket garden, astronaut training simulation rides, and the chance to get up close to the Space Shuttle Atlantis.
Florida Everglades
Kissimmee is near Shingle Creek, the headwaters to the Florida Everglades, sometimes called the Sea of Grass. Kayaking in the calm waters beneath a quiet forest of cypress trees is an ideal way to learn more about this unique ecosystem and the many birds, frogs, and alligators who make it their home. Or take a swamp tour on an airboat and leave the driving to someone else.
Quick stats about vacation rentals in Kissimmee
Total vacation rentals
Explore 7,330 vacation rentals in Kissimmee
Nightly prices starting at
Kissimmee vacation rentals start at $28 CAD per night before taxes and fees
Verified guest reviews
Over 262,660 verified reviews to help you choose
Family-friendly vacation rentals
6,190 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 1,210 rentals that welcome pets
Vacation rentals with a pool
6,620 properties feature pools
Rentals with dedicated workspaces
4,060 properties have a dedicated workspace
Wifi availability
7,280 of Kissimmee vacation rentals include wifi 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Discovery Cove
- Orlando / Kissimmee KOA
- ESPN Wide World of Sports
- 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
- ChampionsGate Golf Club