Find hotels near Waterfront Playhouse, Key West from CA $101

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top Hotels Close to Waterfront Playhouse

Havana Cabana at Key West
Outdoor pool, sun loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1591)
"I Loved everything about it "
The price is CA $186
CA $294 total
includes taxes & fees
Sep 29 - Sep 30
Havana Cabana at Key West
Parrot Key Hotel & Villas
Waterfront King Guest Room | Exterior
Parrot Key Hotel & Villas
4.0 star property
8.8 out of 10, Excellent, (1007)
"This is a beautiful resort! We will definitely be back! Conveniently located. Near Key West airport shopping and entertainment! They offer exiting excursions! It was really neat! My time there was way too short! "
The price is CA $193
CA $290 total
includes taxes & fees
Sep 29 - Sep 30
Parrot Key Hotel & Villas
Casa Marina Key West, Curio Collection by Hilton
Fireplace
Casa Marina Key West, Curio Collection by Hilton
5.0 star property
6.8 out of 10, (1003)
"Beautiful resort and great beach and pool. Staff wonderful. Easy walk downtown!"
The price is CA $404
CA $539 total
includes taxes & fees
Sep 29 - Sep 30
Casa Marina Key West, Curio Collection by Hilton
Southernmost Beach Resort
3 outdoor pools, pool umbrellas, sun loungers
Southernmost Beach Resort
4.0 star property
8.6 out of 10, Excellent, (2130)
"Excellent property in a beautiful area. Attentive and knowledgeable staff. Very clean and well maintained "
The price is CA $362
CA $493 total
includes taxes & fees
Sep 29 - Sep 30
Southernmost Beach Resort
Ibis Bay Beach Resort
Outdoor pool, pool umbrellas, sun loungers
Ibis Bay Beach Resort
2.5 star property
8.0 out of 10, Very good, (1628)
"Very cute spot, beautiful water views and transportation to Duval St was very convenient. "
The price is CA $190
CA $250 total
includes taxes & fees
Oct 2 - Oct 3
Ibis Bay Beach Resort
Winslow's Bungalows - Key West Historic Inns
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns
4.0 star property
9.0 out of 10, Wonderful, (891)
"This was a great stay! We loved the property. Unlike any place we have stayed in the past. The landscape of the place is amazing with trails leading through the property. Cant say enough how accommodating the front desk ladies were upon arrival. Highly recommended! "
The price is CA $265
CA $355 total
includes taxes & fees
Sep 29 - Sep 30
Winslow's Bungalows - Key West Historic Inns
Opal Key Resort & Marina, Key West
Front of property - evening/night
Opal Key Resort & Marina, Key West
4.0 star property
9.0 out of 10, Wonderful, (1002)
"Price, comfort and location. "
The price is CA $350
CA $447 total
includes taxes & fees
Sep 29 - Sep 30
Opal Key Resort & Marina, Key West
Pier House Resort & Spa
View from room
Pier House Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (1005)
"Great location. Beautiful beach. Friendly staff. Clean and comfortable rooms with nice amenities. Great food and drinks."
The price is CA $470
CA $610 total
includes taxes & fees
Oct 1 - Oct 2
Pier House Resort & Spa
Ocean Key Resort - A Noble House Resort
Outdoor pool, sun loungers
Ocean Key Resort - A Noble House Resort
4.0 star property
9.2 out of 10, Wonderful, (1004)
"Sunset pier is the best. "
The price is CA $407
CA $543 total
includes taxes & fees
Oct 9 - Oct 10
Ocean Key Resort - A Noble House Resort
The Reach Key West, Curio Collection by Hilton
Outdoor pool, pool umbrellas, sun loungers
The Reach Key West, Curio Collection by Hilton
4.0 star property
8.4 out of 10, Very good, (761)
"Love that you have access to the Hilton Casa Marina amenities. That place is gorgeous and it was nice to pay the lower price at the curio and be able to use the amenities at casa Marina. Curio was walking distance to everything duvan street has to access and is one of the only properties with its own beach. The room was super spacious! Staff was attentive and friendly. Highly recommend. "
The price is CA $356
CA $485 total
includes taxes & fees
Oct 1 - Oct 2
The Reach Key West, Curio Collection by Hilton
Hyatt Centric Key West Resort and Spa
Exterior
Hyatt Centric Key West Resort and Spa
4.0 star property
9.0 out of 10, Wonderful, (1002)
"Was a very nice stay"
The price is CA $343
CA $474 total
includes taxes & fees
Oct 1 - Oct 2
Hyatt Centric Key West Resort and Spa
Courtyard by Marriott Key West Waterfront
Pool views, open daily
Courtyard by Marriott Key West Waterfront
3.0 star property
8.8 out of 10, Excellent, (1002)
"Good service "
The price is CA $214
CA $241 total
includes taxes & fees
Sep 29 - Sep 30
Courtyard by Marriott Key West Waterfront
Wicker Guesthouse
Porch
Wicker Guesthouse
3.5 star property
8.6 out of 10, Excellent, (1007)
"Parking is on the street, we had to park on a very narrow street and our car was hit 2x. Once dented our rear bumper and the other left a large black mark on our drivers door, good news is the black line can be buffed out. The Bumper needs to be repaired. "
The price is CA $225
CA $253 total
includes taxes & fees
Sep 29 - Sep 30
Wicker Guesthouse
The Palms Hotel
Deluxe King Room (Not Pet Friendly)
The Palms Hotel
3.0 star property
8.4 out of 10, Very good, (1001)
"Had a good stay. Folks were nice and accommodating. The only issue was the resort fee charge. First - I knew about the fee so no gotcha at all. But I was expecting something for the daily fee, Nope.- no restaurant or voucher to neighboring place, the pool bar was closed open, no hotel lobby, no offer of bikes for transportation. I get you can charge it because everyone does but still ....."
The price is CA $196
CA $248 total
includes taxes & fees
Oct 2 - Oct 3
The Palms Hotel
The Marker Key West Harbor Resort
3 outdoor pools, pool umbrellas, sun loungers
The Marker Key West Harbor Resort
4.0 star property
8.8 out of 10, Excellent, (1002)
"Great place. Easy walking to everything. Great staff. "
The price is CA $325
CA $505 total
includes taxes & fees
Sep 29 - Sep 30
The Marker Key West Harbor Resort
Eden House
Pillowtop beds, in-room safe, individually decorated
Eden House
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Very nice property, well maintained. Easy walking distance from the ferry, shopping, and restaurants. The staff, especially Jemma, and Mercedes were awesome. Highly recommend"
The price is CA $236
CA $297 total
includes taxes & fees
Sep 29 - Sep 30
Eden House
NYAH Key West - Adults Only
Outdoor spa tub
NYAH Key West - Adults Only
3.0 star property
7.8 out of 10, Good, (1002)
"Nice place and people."
The price is CA $101
CA $174 total
includes taxes & fees
Sep 30 - Oct 1
NYAH Key West - Adults Only
Lighthouse Hotel - Key West Historic Inns
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Lighthouse Hotel - Key West Historic Inns
3.5 star property
9.0 out of 10, Wonderful, (574)
"Was our first visit to Key West and everything at the Lighthouse was fantastic!!!!! Perfect location, next block over from Duval Directly across the street from Earnest Hemingways home. Continental breakfast was great!!! Staff was very helpful in making suggestions of things to do. Will definitely stay again!!!!!! "
The price is CA $253
CA $341 total
includes taxes & fees
Oct 2 - Oct 3
Lighthouse Hotel - Key West Historic Inns
Fairfield Inn and Suites by Marriott Key West
Outdoor pool, free cabanas, sun loungers
Fairfield Inn and Suites by Marriott Key West
3.0 star property
8.0 out of 10, Very good, (1067)
"This hotel is great!! We have stayed several time and love to come back from time to time!!"
The price is CA $191
CA $253 total
includes taxes & fees
Oct 1 - Oct 2
Fairfield Inn and Suites by Marriott Key West
The Mansion on the Sea - Southernmost House in the USA
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio
The Mansion on the Sea - Southernmost House in the USA
3.0 star property
9.4 out of 10, Exceptional, (1000)
"The Mansion on the sea is a must stay! It’s absolutely a stunning property, amazing ocean views from allover the property. Right in the heart of Duval street. The Staff were hospitable, friendly and professional. I highly recommend this guest house "
The price is CA $605
CA $723 total
includes taxes & fees
Sep 28 - Sep 29
The Mansion on the Sea - Southernmost House in the USA
Don't see what you're looking for?
See all available properties in Waterfront Playhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 1467 hotels and other accommodations you'll find within a mile.

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

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

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

Expedia has 1467 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?

Key West Shipwreck Museum, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Harry S. Truman Little White House, Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters Museum are landmarks to visit in the area. You can watch performances at Red Barn Theater, Key West Burlesque Theater, and Key West Film Society if you're interested in local theater.