Winery Hotels in Kissimmee

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Winery Hotels in Kissimmee

Grand Lake Resort

Kissimmee

CNY479

CNY605 total

includes taxes & fees

Sep 7 - Sep 8

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

CNY629

CNY708 total

includes taxes & fees

Sep 9 - Sep 10

Home2 Suites By Hilton Winter Garden

Winter Garden

CNY717

CNY807 total

includes taxes & fees

Sep 6 - Sep 7

DoubleTree by Hilton Orlando Airport

Airport North

CNY668

CNY751 total

includes taxes & fees

Sep 10 - Sep 11

Homewood Suites by Hilton Orlando-International Drive/Convention Center

International Drive District

CNY563

CNY633 total

includes taxes & fees

Sep 1 - Sep 2

Century Millenia

Florida Center

CNY575

CNY1,151 total

includes taxes & fees

Sep 6 - Sep 7

Home2 Suites By Hilton Winter Haven

Winter Haven

CNY933

CNY1,044 total

includes taxes & fees

Sep 27 - Sep 28

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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 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.

A pier with a lighthouse, palm trees, and a calm body of water.

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, Reunion Resort Golf Course, and ChampionsGate Golf Club are also nearby.

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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 Give Kids the World Village, Lake Buena Vista Factory Stores, and Fun Spot America.

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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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Vintage cars parked on grass under a cloudy sky.

Osceola Heritage Park

7.8/10 (3,681 reviews)

You can catch an event at Osceola Heritage Park, located 2.4 mi (3.9 km) from central Kissimmee. Want to stretch your legs some more? Head to Kissimmee Lakefront Park and Brinson Park, both nearby.

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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 Houston Astros Spring Training, both located nearby.

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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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