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

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

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

Ocean Key Resort - A Noble House Resort

4 out of 5
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

Sunset Key Cottages

2.5 out of 5
245 Front Street Key West FL
0.08 mi from Waterfront Playhouse
Get rates
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

Pier House Resort & Spa

4 out of 5
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

Opal Key Resort & Marina, Key West

4 out of 5
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!

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!

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

Amsterdam's Curry Mansion Inn

3 out of 5
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

Hyatt Centric Key West Resort and Spa

4 out of 5
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

La Concha Key West, Autograph Collection

4 out of 5
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

The Marker Key West Harbor Resort

4 out of 5
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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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.

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

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
The Marker Key West Harbor Resort