Book a hotel near Waterfront Playhouse, Key West Historic District
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Top hotels close to Waterfront Playhouse

Harbor House Suite A | 4 Bed, 4 Bath
Key West FL
0.04 mi from Waterfront Playhouse
$1,288 nightly
The price is $1,420 total per night
$1,420 total
Dec 19 - Dec 20
Total with taxes and fees
This condo features laundry facilities.
Kitchen
Washer

Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath
Key West FL
0.04 mi from Waterfront Playhouse
$1,257 nightly
The price is $1,385 total per night
$1,385 total
Dec 19 - Dec 20
Total with taxes and fees
This vacation home features laundry facilities.
Kitchen
Washer

Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
Free Cancellation
Reserve now, pay when you stay
0.06 mi from Waterfront Playhouse
$614 nightly
The price is $691 total per night
$691 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.
Pool
Spa

Sunset Key Cottages
245 Front Street Key West FL
0.08 mi from Waterfront Playhouse
A private beach, a 24-hour gym, and a restaurant are all featured at this award-winning aparthotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.
Pool
Kitchen

Pier House Resort & Spa
1 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
0.08 mi from Waterfront Playhouse
$361 nightly
The price is $406 total per night
$406 total
Dec 19 - Dec 20
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
On private beach
Pool

Opal Key Resort & Marina, Key West
245 Front Street Key West FL
0.09 mi from Waterfront Playhouse
$434 nightly
The price is $488 total per night
$488 total
Dec 19 - Dec 20
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.
Pool
Hot Tub

Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!
Key West Florida
0.1 mi from Waterfront Playhouse
$430 nightly
The price is $473 total per night
$473 total
Dec 23 - Dec 24
Total with taxes and fees
Stay at this apartment in Key West. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located nearby.
Free WiFi
Air conditioning

The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
Key West FL
0.1 mi from Waterfront Playhouse
$1,101 nightly
The price is $1,210 total per night
$1,210 total
Dec 21 - Dec 22
Total with taxes and fees
Stay at this apartment in Key West. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Duval Street and Mallory Square are located nearby.
Kitchen
Pet friendly

Amsterdam's Curry Mansion Inn
511 Caroline St Key West FL
0.21 mi from Waterfront Playhouse
$335 nightly
The price is $377 total per night
$377 total
Dec 21 - Dec 22
Total with taxes and fees
An area shuttle is featured at this guesthouse, along with an outdoor pool and a terrace. WiFi in public areas is free. A business center, a garden, and a snack bar/deli are also on offer.
Pool
Pet friendly

Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
0.22 mi from Waterfront Playhouse
$382 nightly
The price is $430 total per night
$430 total
Dec 21 - Dec 22
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa

La Concha Key West, Autograph Collection
430 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
0.33 mi from Waterfront Playhouse
$329 nightly
The price is $370 total per night
$370 total
Dec 22 - Dec 23
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly

The Marker Key West Harbor Resort
200 William Street Key West FL
0.37 mi from Waterfront Playhouse
$424 nightly
The price is $477 total per night
$477 total
Dec 21 - Dec 22
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly
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See all available properties in Waterfront Playhouse
View all propertiesLowest 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.
Waterfront Playhouse hotels essential information
Accommodation | 2,750 hotels |
|---|---|
Lowest Price | $370 |
Highest Price | $1,420 |
Popular hotels | Hyatt Centric Key West Resort and Spa, Pier House Resort & Spa, Opal Key Resort & Marina, Key West, Ocean Key Resort - A Noble House Resort, La Concha Key West, Autograph Collection, Amsterdam's Curry Mansion Inn, The Marker Key West Harbor Resort, Harbor House Suite A | 4 Bed, 4 Bath, Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath, Sunset Key Cottages, Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!, The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street! |
Recent Waterfront Playhouse hotel reviews by fellow wanderers

The Marker Key West Harbor Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Pet friendly "
A verified traveler stayed at The Marker Key West Harbor Resort
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