Holiday rentals in Kissimmee

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Top-rated holiday rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Kissimmee
4.89 out of 5 average rating, 61 reviews

The Denmark

The Denmark House it is the perfect home away from home. This lovely home features a lake view, a peaceful private pool area including a hot tub, a game room, and smart TVs. We are Ideally located in Kissimmee just 15-30 minutes from Disney World, Sea World, Universal Orlando, and shopping areas. Pool heating is available upon request (Price varies). Late checkout is available for a $40 fee. BBQ rental available for a $100 fee. All Requests must be submitted at least 24 hours in advance.

Top guest favourite
An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.
Home in Citrus Ridge
5 out of 5 average rating, 59 reviews

Gorgeous 5BR @ Encore Next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 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 HOUSE RULES*

Top guest favourite
A single-story home is presented with a light tan exterior and a welcoming front yard. Lush greenery surrounds the property, featuring neatly trimmed shrubs and palm trees. A paved driveway leads to a two-car garage with solar panels on the roof, providing an energy-efficient touch.
Home in Kissimmee
5 out of 5 average rating, 60 reviews

Family Vacay with Pool near WDW!

We hope to welcome you to this enchanting family retreat in Kissimmee, Florida, just 20 minutes from the magic of Walt Disney World Resort! This sunlit oasis is designed for unforgettable family vacations. Dive into your screened private pool, a cool oasis under the warm Florida sun, to create memories that'll last a lifetime. After an exhilarating day at the parks, return to this cozy home where you'll find the perfect blend of entertainment and relaxation.

Top guest favourite
Flat in Kissimmee
5 out of 5 average rating, 33 reviews

Stay Near Disney w King Bed Amenities PetFriendly

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

Guest favourite
A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.
Home in Citrus Ridge
4.9 out of 5 average rating, 135 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Guest favourite
A spacious entryway features a stylish staircase with wooden steps and a glass railing. A large Christmas tree decorated in soft colors stands next to a modern living area displaying a cozy sofa and contemporary artwork. A fireplace adds warmth to the ambiance.
Home in Citrus Ridge
4.86 out of 5 average rating, 65 reviews

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?

Guest favourite
An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.
Home in Kissimmee
4.79 out of 5 average rating, 132 reviews

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!

Superhost
Home
4.82 out of 5 average rating, 11 reviews

Emerald Island Lake View

Stylish 4 bedroom villa with private pool, completely updated in Nov 24, situated on the fabulously tropical Emerald Island gated resort. The villa has uninterrupted lake views and no rear neighbours, from the deck you can catch the sunset as well as glimpses of Magic Kingdom fireworks each night. Just 10 minutes to Disney and in easy reach of other attractions.

Guest favourite
Home in Kissimmee
5 out of 5 average rating, 7 reviews

9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa

Welcome to your Storey Lake getaway! This spacious 9-bedroom home with a private pool, spa, and game room is designed for unforgettable family vacations—just minutes from Disney, dining, and top attractions. Relax, recharge, and make memories together.

Guest favourite
The spacious living area features a comfortable gray couch adorned with vibrant cushions, complemented by two small tables. A large window provides natural light and a view of the outdoor area with a barbecue and pool, while a wall-mounted TV offers entertainment options.
Townhouse in Kissimmee
4.89 out of 5 average rating, 273 reviews

Luxurious Dream 4/3 Bedroom Home w/private Pool

Located a short 15 minute drive to Disney, this luxury design inspired 4 bedroom, 3.5 bath is perfect for a family, multi family or romantic weekend away with your favourite person.

Superhost
Home in Citrus Ridge
5 out of 5 average rating, 4 reviews

NEW 07 Bedroom Themed Luxury in Solara Resort

* Accommodates: 16 * Bathrooms: 5 * Bedrooms: 07 * Property type: Luxury Villa * Location: Solara Resort

Top guest favourite
Home in Citrus Ridge
5 out of 5 average rating, 12 reviews

2026 Themed 07 Bedrooms/Sleeps 18 At Solara Resort

*The Space * Bathrooms: 7 * Bedrooms: 7 * Property type: Luxury Villa * Location: Solara Resort

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

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Avg. price£106£109£113£110£97£103£109£96£88£93£105£124
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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 the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.

What are the top things to do in Kissimmee?

Old Town

Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.

Fan Boat Swamp Tour

Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.

Hot Air Balloon Ride

Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.

Quick stats about holiday rentals in Kissimmee

  • Total holiday rentals

    Explore 7,330 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 262,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    6,190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,210 rentals that welcome pets

  • Holiday 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 holiday 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee