Historic Downtown Kissimmee Hotels: 2026 Top 10 Historic Downtown Kissimmee Hotels with Limited-Time Deals @Expedia

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

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Where to stay in Historic Downtown Kissimmee

Find the best Historic Downtown Kissimmee areas for the activities you enjoy most.

The entrance to Aquatica with colorful signage and a water slide.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

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

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

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The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

Bay Lake

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

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A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Ample dining options and top golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

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A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

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Top Historic Downtown Kissimmee Hotel Reviews

Walt Disney World Dolphin

10/10 Excellent

"LOVED the WDW perks that came with our hotel (early entry, Disney transportation, etc.), especially at half the price of a WDW resort! S’mores and nightly movies were fun, as well as the $5 arcade credit. Fuel cafe was really convenient with great prices (can’t beat the unweighted $8 froyo+toppings)! There’s also a WDW store inside Dolphin if you need to make any purchases, as well as a general store for everyday necessities. The pool was awesome with plenty of lounge chairs, and the hotel has 4 restaurants. They’re not part of WDW dining plan, but the WDW Boardwalk is only a few mins walk if you need to use gift cards for meals. Some cons: it takes 1-2 transfers to get to the 2 WDW water parks. Typhoon Lagoon was especially difficult bc the bus bays are not marked with hotel names so we didn’t know which bay to wait at, and there’s no instructions once you get off the hotel bus (concierge wasn’t knowledgeable and said the water park directions were handled by a rep from Disney Vacation club, who wasn’t in the lobby when we were inquiring). Disney Springs: the bus back to the hotel is located on the west end of DS, and we weren’t given any instructions so we went back to the east end of DS since that’s where we’d originally been dropped off. It’s about a 15-min walk between east and west. Lastly, hotel was doing some work on the roof (we were on the top floor), and it woke us up @8am on several mornings. Work started on Tues but we didn’t get the notice until Thursday…"

Kompose Boutique Resort at Theme Parks

8/10 Good

"First and foremost, this is a family vacation hotel, and a good one. It has a good complimentary breakfast buffet and a nice pool and pool area as well as a lazy river pool and pickleball court , and gym. I was staying there for business purposes and it is not well suited for that purpose."

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

8/10 Good

"Enjoyed our stay here. For starters, the price was GREAT, 10/10. Location is PRIME!, 10/10. It literally sits in the middle of EVERYTHING (Old Town, LOTS of eateries - including World Food Trucks, shops, grocery stores, etc., etc., etc.). Also, Magic KIngdom, Epcot, Blizzard Beach and other Disney theme parks were only about a 10, maybe 15 minute drive. The outlets and Millenial Mall in Orlando are about 40-45 minutes away, depending on traffic. Check-in was fast & smooth, 10/10. Kudos to the front desk attendant. He, along with the other staff, provided great CS, 10/10. Cleanliness, 9/10. We had to change rooms because the original room we were given was not ready for guests. Again, the desk attendant took good care of us expeditiously and with great customer care. Breakfast, for me, 0/10, do not recommend. Family-friendly, 10/10. My only major complaint is it's a smoke free hotel, but clearly smoking was being done inside the hotel. I know you can't control everything, but maybe walk the floors, get on the elevator and assess. The smell was very strong in the elevators, on the floor of the 1st room we had and it came through to our room in the 2nd room we had, especially early in the mornings. I did not like that. The hotel is dated, but the upkeep is very good. For the amount paid, it was luxury. In total, 7/10. Not a bad stay, just hated the smell of smoke inside the hotel. Other than that, I would definitely recommend."

The Grove Resort & Water Park Orlando

10/10 Excellent

"This is our second year staying at The Grove. The space is excellent, and one of the few places that offers a full kitchen with 2 bedrooms and 2 bathrooms, and laundry within the room. The pools and arcade are a hit with the kids. I was expecting housekeeping services at least once during our week stay, but no one came. But I don't mind cleaning, and the room has laundry anyway."

Frequently asked questions

What is Historic Downtown Kissimmee like?

Historic Downtown Kissimmee is a neighbourhood that people enjoy for its major shopping area. Make sure that you visit Osceola County Clerk of the Court and Lake Tohopekaliga as part of your Historic Downtown Kissimmee travel plans.

Where is the best place to stay in Historic Downtown Kissimmee?

Based on Expedia customer reviews, Kapp and Kappy B&B is the highest ranked property in Historic Downtown Kissimmee. This B&B offers free breakfast and free parking.

How many hotels will I be able to find in the Historic Downtown Kissimmee area?

If you're searching for places to stay in Kissimmee, Expedia has something to meet your needs with 82 Historic Downtown Kissimmee hotels and other accommodation options to choose from.

If I need to cancel my hotel reservation in Historic Downtown Kissimmee, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of booking. Put your dates in and click on "Search", then filter by "fully refundable" to get the top deals on offer in Historic Downtown Kissimmee.

What is there to do around this Kissimmee neighbourhood?

Spend some time exploring the natural setting of Historic Downtown Kissimmee with a visit to Kissimmee Lakefront Park and Lake Tohopekaliga. Osceola County Clerk of the Court and Kissimmee Civic Center are also a couple of places to visit in the neighbourhood. A few places to visit in the area around Historic Downtown Kissimmee include Violet's Venom Brewery, Monument of States and Bataan-Corregidor Memorial. While you're out sightseeing in Kissimmee, make sure that you visit other sights such as Brinson Park or Big Toho Marina.

How can I get around Historic Downtown Kissimmee and the greater Kissimmee area?

To venture out of town, take a train from Kissimmee Station.

Historic Downtown Kissimmee hotels in Orlando

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Our top choices for Historic Downtown Kissimmee hotels

Super Boho Waterfront Retreat w Fishing Views

Kapp and Kappy B&B

Super Boho - At Lake Toho Fishing Vintage Vibes

Super Boho- At Lake Toho s Water Sleeps 6

Boho Lake Fishing Civic Center More

Lake Toho Parks Pool Fishing Sleeps 8

Super Boho - Lake Toho Timeless Charm

Kompose Boutique Resort at Theme Parks

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Hyatt House Orlando International Drive

La Quinta Inn & Suites by Wyndham Orlando Airport

Hyatt Regency Orlando International Airport

EVEN Hotel Orlando International Airport by IHG

Courtyard by Marriott across Universal Orlando

Wyndham Garden Orlando Airport

Vacation Village Orlando, Celebration

Wingate by Wyndham - Orlando International Airport

Margaritaville Resort Orlando with H2O Waterpark

Rosen Shingle Creek

Hyatt House Orlando Airport

Where to stay in Historic Downtown Kissimmee

International Drive District

Reunion

Bay Lake

Champions Gate

Florida Center

Top Historic Downtown Kissimmee Hotel Reviews

Walt Disney World Dolphin

Frequently asked questions

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