The Best Hotels Closest to Waterfront Playhouse in Key West for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Compare popular hotels close to Waterfront Playhouse

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,007 reviews	View
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 1,000 reviews	View
Alexander's Guesthouse - Adult Exclusive	3.5 star property	9.8 Exceptional 176 reviews	View
The Conch House Heritage Inn	3.5 star property	9.8 Exceptional 198 reviews	View
Duval House	3.0 star property	9.6 Exceptional 1,139 reviews	View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

Ocean Key Resort - A Noble House Resort

Key West Historic District

NT$12,058 total

includes taxes & fees

Nov 29 - Nov 30

Other attractions near Waterfront Playhouse

A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 reviews)

This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.

See properties

Top Waterfront Playhouse Hotel Reviews

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

Artist House Key West

Key West Historic District

10/10 Excellent

Anonymous traveler

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

The Gardens Hotel

Old Town Key West

10/10 Excellent

Anonymous traveler

A modern interior with a staircase, a sofa set, a wooden table, and a television.

Simonton Court Historic Inn & Cottages

Key West Historic District

10/10 Excellent

RADANA

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

Key West Villas

Old Town Key West

10/10 Excellent

Thys

A two-story house with a covered porch, a brick pathway, and a large tree.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

A tropical outdoor area with palm trees, hanging plants, and string lights.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

Anthony

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

10/10 Excellent

Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.

Dominick

A porch with a white railing, a bench, and a flag.

The Conch House Heritage Inn

Old Town Key West

10/10 Excellent

Nicholas

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

Keith

A swimming pool with lounge chairs and a bar area.

H2O Suites - Adults Only

Old Town Key West

10/10 Excellent

My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...

Erin

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

Duval House

Old Town Key West

10/10 Excellent

The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...

Sarah

A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.

Weatherstation Inn

Old Town Key West

10/10 Excellent

Tucked into the very quiet Truman Annex, the Weatherstation Inn was a great find. It is an old house, built in 1911. If you enjoy old, quiet inns with reconfigured spaces, then this is the place for you. If you are looking for uniform, sleek and modern, then head on down the road. The continental breakfast was just right with delicious pastries from local bakery and the bed was comfy. Perhaps the most perfect aspect of the inn is the parking space where we parked our vehicle upon arrival and did...

GaGirlWalking

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

The Grand Guesthouse

Old Town Key West

10/10 Excellent

The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area. The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed! Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...

Anonymous traveler

A green house with a white porch, a flag, and a sign advertising a property for sale.

L'Habitation Guest House - Adults Only

Key West Historic District

10/10 Excellent

Anonymous traveler

A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

Ambrosia Key West

Old Town Key West

10/10 Excellent

Anonymous traveler

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late! When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...

Val

Frequently Asked Questions

What's the area like around Waterfront Playhouse?

Waterfront Playhouse is located in an area of Key West known for its beautiful ocean views, sailing, and lively festivals. If you're looking for a convenient place to stay, check out the 1400 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Waterfront Playhouse?

Adjacent to Waterfront Playhouse, Pier House Resort & Spa is one of the top choices for your stay based on our traveler data, and this resort offers a full-service spa and a private beach. Other good options within a short distance include Hyatt Centric Key West Resort and Spa and Opal Key Resort & Marina, Key West.

How many hotels will I be able to find near Waterfront Playhouse?

Expedia has 1400 hotels and other accommodations within a mile from Waterfront Playhouse.

If I need to cancel the hotel reservation for my stay near Waterfront Playhouse, will I receive a refund?

Yes, you'll find most hotel reservations are refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Add your dates and click on "Search", then you can use the "fully refundable" filter to get the top deals on offer near Waterfront Playhouse.

Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?

To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/.

What can I see and do near Waterfront Playhouse?

Harry S. Truman Little White House, Florida Keys Eco - Discovery Center, and Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Key West Lighthouse and Keeper's Quarters Museum, Fort Zachary Taylor Historic State Park, and Fort East Martello Museum and Gallery are landmarks to visit in the area. You can watch performances at Red Barn Theater, Key West Film Society, and The Key West Theater if you're interested in local theater.

Find hotels near Waterfront Playhouse, Key West from NT$5,554

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. Simonton Court Historic Inn & Cottages

3. Alexander's Guesthouse - Adult Exclusive

4. The Conch House Heritage Inn

5. Duval House

6. Island City House Hotel

7. Santa Maria Suites

8. L'Habitation Guest House - Adults Only

9. Weatherstation Inn

10. Westwinds Inn

11. Coco Plum Inn

12. Alexander Palms Court

13. Silver Palms Inn & Historic Homes

14. Heron House - Adult Only

15. Hyatt Centric Key West Resort and Spa

16. The Marker Key West Harbor Resort

17. The Garden House

18. Paradise Inn Key West - Adults Only

19. Opal Key Resort & Marina, Key West

20. The Key West Hotel

Compare popular hotels close to Waterfront Playhouse

Hotels recommended for families near Waterfront Playhouse

Ocean Key Resort - A Noble House Resort

Other attractions near Waterfront Playhouse

Key West Shipwreck Museum

Top Waterfront Playhouse Hotel Reviews

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Frequently Asked Questions

What's the area like around Waterfront Playhouse?

What's the best hotel to stay near Waterfront Playhouse?

How many hotels will I be able to find near Waterfront Playhouse?

If I need to cancel the hotel reservation for my stay near Waterfront Playhouse, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?

What can I see and do near Waterfront Playhouse?

Explore a world of travel with Expedia