5 Star Hotels in Kissimmee

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

5 best 5 Star Hotels in Kissimmee at a glance

Encore Resort and Water Park at Reunion by Rentyl — 5-star hotel in Kissimmee. Guest rating: 8.4/10 — Very Good.
ette hotel — 5-star hotel in Kissimmee. Guest rating: 9.6/10 — Exceptional.
Reunion Resort & Golf Club — 5-star hotel in Reunion. Guest rating: 8.8/10 — Excellent.
The Ritz-Carlton Orlando, Grande Lakes — 5-star hotel in Orlando. Guest rating: 9.2/10 — Wonderful.
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel — 5-star hotel in Orlando. Guest rating: 9.4/10 — Exceptional.

5 Star Hotels in Kissimmee

A large, multi-story hotel with a central entrance, multiple wings, and a clock tower.

A spacious lobby with a central reception desk, a staircase, and a view of the outside.

A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

$220

$783 total

includes taxes & fees

Sep 14 - Sep 15

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.

A restaurant interior with wooden tables and chairs, a marble wall, and a seating area with a cushioned bench.

A person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.

ette hotel

Kissimmee

$253

$287 total

includes taxes & fees

Sep 19 - Sep 20

An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

A spacious lobby with a grand chandelier, a piano, and a reception desk.

A patio area with wicker furniture, a fire pit, and palm trees.

A multi-story hotel with a central courtyard, a bell tower, and a covered entrance.

Reunion Resort & Golf Club

Reunion

$263

$346 total

includes taxes & fees

Aug 31 - Sep 1

A water park with multiple slides and a pool area surrounded by palm trees and a golf course.

A spacious lobby with a high ceiling, large windows, and a variety of seating arrangements including sofas and armchairs.

A modern living room with a sofa set, coffee table, and decorative plants.

A dining area with tables set for service, large arched windows, and wall-mounted lighting.

The Ritz-Carlton Orlando, Grande Lakes

Orlando

$375

$484 total

includes taxes & fees

Sep 12 - Sep 13

A hotel with a swimming pool, lounge chairs, and palm trees.

A long dining table set with chairs, surrounded by hanging lights and greenery.

A grand lobby with a central clock, a chandelier, and a patterned floor.

A spacious hotel corridor with large windows, a blue carpet, and elegant chandeliers.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

$259

$348 total

includes taxes & fees

Aug 31 - Sep 1

A resort with multiple swimming pools, lounge areas, and a modern building with balconies.

A rooftop lounge with wicker furniture, round tables, and potted plants.

A spacious lobby with a view of a body of water, large wooden columns, and a modern tiled floor.

A modern hotel entrance with a large wooden ceiling structure, glass doors, and a view of the outdoors.

Conrad Orlando at Evermore

Orlando

$496

$608 total

includes taxes & fees

Sep 6 - Sep 7

A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.

A pathway lined with tall, vertically planted trees and well-maintained greenery, leading towards a building with classical architecture.

An indoor dining area with multiple tables and chairs, large windows, and a bar counter.

A hotel with a central courtyard, a reflective pool, and a large building with a prominent entrance.

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Golden Oak

$940

$1,119 total

includes taxes & fees

Sep 2 - Sep 3

A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

A hotel with a blue exterior, white railings, and a well-maintained garden with a central flower bed.

A restaurant with round tables, wooden chairs, and large windows.

A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.

Disney's Beach Club Resort

Bay Lake

$434

$488 total

includes taxes & fees

Aug 31 - Sep 1

A row of white buildings with balconies, connected by a walkway with string lights and street lamps.

A large, multi-story building with balconies and a waterfront view.

Disney's Beach Club Villas

Bay Lake

$1,776

$1,998 total

includes taxes & fees

Sep 12 - Sep 13

See more properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Keep exploring

More ways to book

Book 5 Star Hotels in Kissimmee on Hotels.com