Casino Hotels in Kissimmee

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Casino Hotels in Kissimmee

A spacious living room with a large window, a white sofa, a glass coffee table, and a small side table.

A hotel with a swimming pool, palm trees, and a covered walkway.

A glass-enclosed shower with a handheld showerhead, a towel rack, and a towel hanging on the glass door.

A modern kitchen with a stainless steel refrigerator, microwave, and dishwasher. There are wooden shelves above the counter and a small sink area.

1. Ramada by Wyndham Davenport Orlando South

Davenport

$71

$80 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

A spacious hotel lobby with multiple round tables and chairs, elegant chandeliers, and framed artwork on the walls.

A spacious lobby with a seating area, a marble coffee table, and a staircase leading to an upper floor.

A spacious lobby with modern furniture, a staircase, and multiple hanging light fixtures.

2. The View Hotel, Trademark Collection by Wyndham

Orlando

$78

$87 total

includes taxes & fees

Sep 29 - Sep 30

A reception area with a modern design, featuring a counter with a textured panel, a large abstract artwork on the wall, and a coffee station with various items.

A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a small covered seating area.

3. Best Western Auburndale Inn & Suites

Auburndale

$101

$113 total

includes taxes & fees

Oct 1 - Oct 2

A golf course with a swimming pool, a pond, and a clubhouse.

A two-story building with a balcony, a covered entrance, and a well-maintained garden with a tree and various plants.

A fitness center with treadmills, elliptical machines, and a stair climber.

A building with a central atrium, a palm tree, and a brick floor.

4. 3919 Orlando Vacational Apartment

Ventura

A modern living room with a black leather sofa, a grey armchair, a wooden coffee table, and a flat-screen TV mounted on the wall.

A modern building with a courtyard featuring a central plant, a staircase, and a door marked with the number 107.

A room with a bunk bed, a window with blinds, a bedside table with a lamp, and a wall clock.

A modern two-story building with a covered outdoor area and a well-maintained lawn.

5. 3697 Orlando Vacational Apartment 1st floor near Universal Studios

Ventura

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Top neighborhoods in Kissimmee

A golf course with bunkers, water hazards, and a large lake.

A golf course with sand bunkers, a water hazard, and a clubhouse in the background.

A large body of water surrounded by green vegetation and trees under a partly cloudy sky.

A white bird flying over a body of water with dense green foliage in the background.

A waterfront hotel with a prominent tower and multiple buildings along the shore.

Reunion

Reunion is a golfer's paradise just outside Orlando with three legendary courses designed by Palmer, Nicklaus, and Watson. After teeing off, splash around at the resort water park or lounge by multiple pools scattered throughout this upscale community. When you're ready for theme parks, Disney and Universal are just 20 minutes away. Vacation homes with private pools dominate the accommodation scene, giving families plenty of space to spread out. Resort restaurants serve upscale meals, though you'll need a car to explore beyond the community's Mediterranean-style grounds. The quiet, manicured setting feels worlds away from Orlando's tourist bustle.

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A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

A yellow vintage car driving down a brick-paved street lined with a black metal fence and green benches.

A lighthouse by a calm lake, surrounded by trees and a grassy area.

A green-roofed building with a covered porch, surrounded by trees and a well-maintained lawn.

A castle-like structure with the words "Medieval Times" on the top.

Historic Downtown Kissimmee

Historic Downtown Kissimmee captures Florida's past with its stunning 1890s courthouse and Victorian storefronts along Broadway Street. Stroll under heritage oaks while exploring unique shops filled with antiques and local crafts. Weekend farmers markets and street festivals bring the area to life, celebrating the region's cowboy heritage and diverse community. The lakefront area offers peaceful fishing spots and scenic views of Lake Tohopekaliga. A mix of Southern comfort food, Cuban cafes, and barbecue joints fuel your adventures. Most attractions are within the walkable six-block historic core, making it easy to explore this charming slice of old Florida.

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An aerial view of a residential area with numerous houses, roads, and several lakes.

A tree with hanging moss and green leaves against a clear blue sky.

A city skyline reflected in a calm lake with modern buildings and trees along the shore.

A palm tree with a brown trunk and red foliage, surrounded by green leaves and red flowers.

Orlando skyline with fireworks, theme park rides, and a castle.

Windsor Hills

Windsor Hills offers a perfect home base for Disney adventures with resort-style amenities just minutes from major attractions. Families love the gated communities with pools, game rooms, and themed vacation rentals ranging from cozy condos to luxury villas. After exhilarating theme park days, this quiet residential haven provides a peaceful retreat. Dining options are limited within the neighborhood, so most visitors drive 10-15 minutes to nearby tourist areas for meals. Rental cars are essential for getting around, though rideshares are readily available. The Mediterranean-style properties with private pools make Windsor Hills ideal for groups seeking comfort between park visits.

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A sunset over a marshy landscape with a wooden pier extending into the water.

An aerial view of a resort with multiple buildings, a lake, and golf courses.

A sunset over a calm lake with a pier and reeds in the foreground.

A sunset over a calm body of water with a silhouette of trees in the background.

A sunset over a lake with a boat and a forested shoreline.

Orange Lake

Orange Lake revolves around vacation vibes with the massive Orange Lake Resort at its center. Championship golf courses, sparkling pools, and family-friendly recreation areas keep visitors entertained without leaving the neighborhood. Disney World is just minutes away, making this Four Corners spot perfect for theme park enthusiasts who want amenities galore after a day of adventure. Resort shuttles and rideshares make getting to attractions easy since public transit is limited. Dining options stick mostly to resort restaurants and nearby chains. Vacation villas and timeshare units dominate the accommodation scene, offering spacious digs with full kitchens and multiple bedrooms for families.

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A lakeside town with a prominent white building, lush greenery, and a distant city skyline.

Lake Berkley

Kissimmee's Lake Berkley neighborhood offers attractions including beach near Lake Berkley.

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Top landmarks in Kissimmee

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)

Why not give yourself a treat with a trip to Old Town, one of the most popular family attractions located 7.1 mi (11.4 km) from central Kissimmee. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you have fun at Old Town, you'll love Fun Spot America, just a short walk away.

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A golf course with sand bunkers, trees, and a flagstick.

Mystic Dunes Golf Club

7.8/10 (4,134 reviews)

You might want to play some rounds at Mystic Dunes Golf Club, located 2 mi (3.3 km) from central Four Corners. If Mystic Dunes Golf Club doesn't quite scratch your golfing itch, Orange Lake Golf, and Reunion Resort Golf Course are also nearby.

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A water park with a pool, palm trees, and a statue of a horse.

Kissimmee Lakefront Park

8.4/10 (2,921 reviews)

Kissimmee Lakefront Park is worth a pic or two when discovering Historic Downtown Kissimmee.

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Silver Spurs Arena

7.8/10 (3,021 reviews)

You can catch an event at Silver Spurs Arena, located 2.3 mi (3.7 km) from central Kissimmee. If you think Silver Spurs Arena is cool, you also might like Osceola Heritage Park and The Ice Factory of Central Florida, both located nearby.

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A landscape with a clear blue sky, a large body of water with lily pads, and a distant horizon.

Boggy Creek Airboat Rides

7.8/10 (463 reviews)

Why not give yourself a treat with a trip to Boggy Creek Airboat Rides, one of the family attractions located 11 mi (17.6 km) from central Kissimmee. If you'd also like to explore some of the parks in Kissimmee, head to Lakefront Park.

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Three heraldic shields on a wall covered in ivy.

Medieval Times

8.0/10 (3,178 reviews)

Medieval Times is 3.5 mi (5.6 km) from central Kissimmee, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to experience more of the culture Kissimmee has to offer, head to 192 Flea Market, Give Kids the World Village, and Lake Buena Vista Factory Stores.

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Reunion Resort Golf Course

7.6/10 (3,040 reviews)

You might want to play some rounds at Reunion Resort Golf Course, located 11.1 mi (17.9 km) from central Kissimmee. If Reunion Resort Golf Course doesn't quite scratch your golfing itch, ChampionsGate Golf Club, and Mystic Dunes Golf Club are also nearby.

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Island H2O Live!

8.2/10 (270 reviews)

If thrills are what you're after, head to Island H2O Live!, located 1.8 mi (2.8 km) from central Four Corners. If you have fun at Island H2O Live!, you'll love Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios®, both located nearby.

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