Historic Hotels in Kissimmee

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Historic Hotels in Kissimmee

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Kissimmee on Hotels.com. These Kissimmee Historic Hotels consistently deliver on quality, location and traveler experience. Last updated on October 12, 2026.

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

A pool area with a chandelier, a statue, and a view of the outside.

A modern hotel with a central pool area featuring a red boat and palm trees.

A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.

1. Kompose Boutique Resort at Theme Parks

Kissimmee

CNY174

CNY494 total

includes taxes & fees

Oct 13 - Oct 14

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

An outdoor seating area with wicker furniture, a central wooden table, and a red brick wall with potted plants.

A hotel with a swimming pool, multiple parking spaces, and a view of the surrounding area.

A hotel room with a bed, a sofa, a coffee table, a TV, and a desk with a computer.

2. Seasons Florida Resort

Kissimmee

CNY300

CNY341 total

includes taxes & fees

Oct 14 - Oct 15

A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

A modern kitchen with white countertops, stainless steel appliances, and hanging plants.

A swimming pool with clear water, surrounded by a white fence and shaded by several white umbrellas.

A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.

3. Palazzo Lakeside Hotel

Kissimmee

CNY186

CNY439 total

includes taxes & fees

Oct 13 - Oct 14

A living room with patterned chairs, a red sofa, a wooden coffee table, and a decorative wall piece.

A hotel room with two beds, a desk with a TV, a chair, and a window with curtains.

A hotel reception area with a wooden reception desk, a seating area with patterned chairs, and a staircase leading to an upper level.

A restaurant with multiple tables and chairs, a kitchen area, and a large window providing a view of the outside.

4. Quality Inn & Suites Heritage Park

Kissimmee

CNY369

CNY419 total

includes taxes & fees

Nov 8 - Nov 9

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

A spacious outdoor area with multiple white tables and planters, a central digital display, and a modern architectural design.

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

An outdoor dining area with round tables covered in foliage, surrounded by chairs, and a stone wall with plants.

5. Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

CNY734

CNY833 total

includes taxes & fees

Oct 18 - Oct 19

A hotel with a central entrance, palm trees, and a clear sky.

A hotel lobby with seating areas, a reception desk, and a Coca-Cola refrigerator.

A hotel room with two beds, a large window with curtains, an air conditioning unit, and a bedside table with a lamp.

A multi-story hotel with a swimming pool surrounded by palm trees and greenery.

6. Comfort Suites Maingate East

Kissimmee

CNY503

CNY571 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a sofa, a desk with a TV, a bed, and a view of a building with balconies.

A hotel lobby with a bar area, multiple seating arrangements, and a large window providing a view of the outdoors.

A large hotel with multiple floors, a well-lit entrance, and a landscaped driveway.

A poolside area with a lounge chair, a small table, and a covered seating area.

7. Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Kissimmee

CNY421

CNY578 total

includes taxes & fees

Oct 15 - Oct 16

A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.

A view from a balcony with a table and chairs, overlooking a courtyard with palm trees and buildings.

The Club Sevilla building with a covered entrance, palm trees, and flower beds.

A hotel room with a large bed, a television, a wardrobe, a bathroom with a bathtub, and a kitchenette.

8. Club Sevilla

Kissimmee

CNY337

CNY418 total

includes taxes & fees

Oct 13 - Oct 14

A hotel with a pool, outdoor seating, and a sign for 'Galleria'.

A hotel room with a bed, desk, chair, and a TV on the wall.

An aerial view of a swimming pool with lounge chairs and a small waterfall feature.

A dining area with wooden tables and chairs, a reception desk, and a television screen.

9. Galleria Palms Hotel

Kissimmee

CNY392

CNY593 total

includes taxes & fees

Oct 13 - Oct 14

A modern living room with a stone fireplace, comfortable seating, and large windows offering a view of greenery.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A corner market with refrigerated beverage and snack shelves, wooden paneling, and a sign indicating the location.

10. Fairfield Inn and Suites Orlando Kissimmee Celebration

Kissimmee

CNY576

CNY654 total

includes taxes & fees

Oct 28 - Oct 29

An outdoor patio area with wicker furniture, a fire feature, and umbrellas.

A poolside area with lounge chairs, a table, and umbrellas.

A hotel room with two beds, a TV, a desk, and a window with curtains.

A spacious lobby with a reception desk, seating area, and a bar.

11. Nobile Hotel Parkway at Celebration Orlando

Kissimmee

CNY270

CNY511 total

includes taxes & fees

Oct 13 - Oct 14

A pool with a waterfall feature, surrounded by palm trees and a rocky landscape.

An aerial view of a hotel complex with multiple buildings, a swimming pool, and two ponds.

A bar area with a counter, blue chairs, and hanging wicker lamps.

A modern kitchen with a marble island, blue cabinets, and a variety of food items on shelves.

12. Delta Hotels by Marriott Orlando Celebration

Kissimmee

CNY448

CNY699 total

includes taxes & fees

Oct 14 - Oct 15

A spacious lobby with a central seating area, large windows, and potted plants.

A modern dining area with white tables and yellow chairs, large windows, and a green wall.

The entrance of Park Royal Orlando with a paved walkway, potted plants, and a bench.

A modern living room with a round dining table, a sofa, and a TV mounted on the wall.

13. Park Royal Orlando managed by Accor

Kissimmee

CNY301

CNY342 total

includes taxes & fees

Nov 4 - Nov 5

A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

A hotel room with a flat-screen TV, a desk with a lamp, a chair, a sofa, and a sliding glass door leading to a balcony.

A modern hotel room with a kitchenette, a sofa, a coffee table, a TV mounted on the wall, and a patterned rug.

A restaurant with a mural of a beach scene, wooden tables and chairs, and a bar area with bottles.

14. Radisson Hotel Orlando Lake Buena Vista South

Kissimmee

CNY313

CNY507 total

includes taxes & fees

Nov 5 - Nov 6

A room with a black door, a large window, and a view of a swimming pool and buildings.

A modern dining area with long tables and chairs, large windows, and potted plants.

A modern bedroom with a large bed, bedside tables, a desk, and a TV.

15. The Vietta Hotel

Kissimmee

CNY381

CNY584 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with two beds, a chair, and artwork on the walls.

A motel with a covered parking area, a red pickup truck, and a palm tree.

A corner room with a patterned armchair, a blue wall, and a framed artwork.

A bathroom with a toilet, a shelf with towels, and a shower curtain.

16. Soho Inn & Suites

Kissimmee

CNY271

CNY308 total

includes taxes & fees

Oct 18 - Oct 19

A pool area with lounge chairs and palm trees.

A spacious lobby with a curved red sofa, round wooden coffee tables, and a variety of seating options including chairs and armchairs.

A hotel with a prominent entrance, a flag, and palm trees.

17. SpringHill Suites by Marriott Orlando Lake Buena Vista South

Kissimmee

CNY530

CNY602 total

includes taxes & fees

Oct 18 - Oct 19

A spacious dining area with a long table and multiple seating options, including booths and chairs.

A hotel entrance with a covered patio, columns, and a glass door leading inside.

A modern living room with a curved leather sofa, a round glass coffee table with a plant, and a chandelier with two decorative rings.

A modern kitchen with a sink, dishwasher, microwave, and a round mirror above the counter. There is a dining table with chairs and a coffee machine on the counter.

18. Quality Inn & Suites By the Parks

Kissimmee

CNY502

CNY570 total

includes taxes & fees

Oct 26 - Oct 27

A modern hotel lobby with a stone wall, a flat-screen TV, a yellow sofa, teal armchairs, a reception desk, and a digital information kiosk.

A multi-story hotel with a red roof, a central tower, and a landscaped courtyard.

A modern lobby with a stone wall, a flat-screen TV, a green and yellow sofa, and a blue armchair.

A hot tub surrounded by a pool, outdoor seating, and palm trees.

19. Best Western Plus Orlando Lake Buena Vista South Inn & Suites

Kissimmee

CNY438

CNY573 total

includes taxes & fees

Nov 2 - Nov 3

A hotel entrance with a pool, palm trees, and a fountain.

A courtyard with a fire pit, surrounded by a brick wall, and a pool in the background.

A pool area with a gazebo, palm trees, and a building in the background.

A spacious food court with multiple counters, hanging lights, and a central decorative feature.

20. Ramada by Wyndham Kissimmee Gateway

Kissimmee

CNY351

CNY536 total

includes taxes & fees

Nov 5 - Nov 6

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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 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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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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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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Give Kids the World Village

7.8/10 (1,311 reviews)

Why not give yourself a treat with a trip to Give Kids the World Village, one of the family attractions located 3.1 mi (5 km) from central Kissimmee. If you have fun at Give Kids the World Village, you'll love Old Town and Fun Spot America, both located nearby.

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