Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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(Discounted Rates) Vacation Home (4 Miles Disney)
We have the perfect vacation home for You! Fully equipped 3 bedroom home with patio and pool overlooking a pond and conservation area. Just a 10 minute drive from Disney yet in a quiet gated community with playground. Sleeps 6 guests in 3 bedrooms. All beds are new, including king size bed in master bedroom. Folding cots and full size folding crib are available. Master bedroom has a private master bath. Close to local shopping ,dining and attractions. Request heated pool for additional fee.
Cozy Disney Oasis Pool Home 10 Mins from Parks!
Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!
Private Pool & Free Heat - Close to Disney!
3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms
Stylish Villa Private Pool-SPA Near Parks Disney!
Stylish villa 4 bed/3 bath family home with private facing pool & SPA, living room, family room, kitchen, breakfast bar, dining table, a game room, Wi-Fi, smart TVs, wheelchair accessible, close to the parks, shops, and restaurants, Pool & SPA heater at additional cost, located at Glenbrook community. We have it all and much more to enjoy. The pool & SPA heater fee is $25 (USD) per day. The BBQ grill is an additional $45 (USD) charge for the whole stay, including 1 propane gas and cleaning.
Intense Space-Themed Condo Near Disney
Make this newly renovated luxury condo your launching pad for your next intergalactic adventure! Enjoy custom lighting and artwork inspired by Galaxy's Edge, set in the midst of mature trees, lakes, and wildlife. Between ventures, relax at any of four pools, six hot tubs, and a beach with a fishing dock. Hit a few balls on the tennis and pickleball court or shoot some hoops, then cool off at the splash pad, dine at the Tradewinds restaurant, or rejuvenate at the Cenote spa, all on-site.
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.
Cozy Themed Villa 6 BR | Close to Disney
🏖️☀️🏄♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!
Family Villa w/ PS5 + Pvt Pool + BBQ | Near Disney
Welcome to your dream vacation villa just minutes from Disney! Nestled in the prestigious Windsor at Westside, this 6-bedroom retreat is perfect for families and large groups. Enjoy a private southwest-facing pool, barbecue grill, and fully equipped kitchen. Kids will love the Minions and Mickey-themed bedrooms, while everyone can unwind with the PlayStation 5 and smart TVs. Close to Orlando’s top restaurants, shops, and attractions, this home blends comfort, fun, and convenience.
Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.
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!
4809 - 5BR w/ Pool | 10 min Disney | 2 Water Parks
Enjoy comfort, style, and location at this 5-Bedroom / 5-Bathroom single-family resort pool home in Storey Lake. Features 2 King en-suites, 1 King bedroom, Star Wars and Mickey themed bedrooms, fully stocked kitchen, open living area, and private pool and spa (hot tub). Resort amenities include pools, lazy river, slides, splash pad, fitness center, and sports courts—all minutes from Disney, Universal, and shopping.
Movie Room | Hot Tub | Sunny Pool | Fun House
• 4BR | 3BA | Sleeps 9 – 2 king suites + kids’ bunk room • Private sunny pool & FREE heated hot tub • Movie room with cinema seating, popcorn maker & mini fridge • Games area with pool table for family fun • Two living areas + fully equipped kitchen • Quiet, family-friendly location near Disney & Universal • Close to ChampionsGate golf, shopping & restaurants • 🎁 Complimentary welcome pack on arrival
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee
4 Season Vacay, Near Disney, King Bed ste
The Disney House • Immersive Rooms • Gaming Lounge
Modern King Apt w Water view, Pool Gym Near Parks
Brand New 12br/33 ppl-Pool/Arcade/Theatre
8 BD/ 8 BA Sleeps 21! Encore At Reunion (7714 FD)
FL Palm Vibes-4 Bdrm Pool- Perfect for Family
Disney Mega Villa • Escape Rm • Cinema • Pool
Boutique Luxury Home, Private Pool Close to Disney
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
Your Family's Disney HQ~Sleeps 8~No Extra Fees!
Charming Villa near Disney, pool, 3 beds, sleeps 5
Beach Resort with pool tiki bar near Disney World
Family friendly vacation rentals in Kissimmee
No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291
All 5 star stay with Waterpark, GameRm, Ariel Buzz
Mickey Fantasia Family Friendly w/accessibility
OMG! Disney Area, Movie Theater, Game Room & Pool!
Magical Pool Villa-close to Disney Game/movie Room
Game & Theater Room, Castle Bunks, Pool & Spa
Be Our Guest !
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$29,346 GYD | G$30,178 GYD | G$31,427 GYD | G$30,595 GYD | G$27,057 GYD | G$28,722 GYD | G$30,387 GYD | G$26,640 GYD | G$24,559 GYD | G$25,808 GYD | G$29,138 GYD | G$34,341 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 7,330 vacation rentals in Kissimmee
Nightly prices starting at
Kissimmee vacation rentals start at G$4,163 GYD 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 & 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
Wi-Fi availability
7,280 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
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Give Kids the World Village
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Shingle Creek Golf Club
- Universal's Islands of Adventure