Hotels in Waterfront Playhouse, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Hotels
  3.  USA

  4.  Florida

  5.  Key West
  6.  Waterfront Playhouse

Refine your search

Price per night

Amenity Filter

Rating

254 Best Hotels in Waterfront Playhouse (Starting from $256)

Classic King Balcony at the James House
Classic King Balcony at the James House
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

8.7

Fabulous

9 reviews

$469
Average price / night
Check Availability
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
Hotel
245 Front Street, Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Bar, Breakfast Available, Business Services, Elevator, Fitness Equipment, Frontdesk 24 Hour, Hot Tub, Laundry

9.2

Superb

1081 reviews

$431
Average price / night
Check Availability
Hyatt Vacation Club at Sunset Harbor
Hyatt Vacation Club at Sunset Harbor
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

Accommodations, Parking, 4-star, Lodgings, Places to stay, Self-catering, Accessible hotels

8.2

Very Good

173 reviews

$323
Average price / night
Check Availability
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1293
Average price / night
Check Availability
King Suite at Curry Mansion with Heated Pool!
King Suite at Curry Mansion with Heated Pool!
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

8.2

Very Good

35 reviews

$273
Average price / night
Check Availability
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1298
Average price / night
Check Availability
Deluxe King with Balcony - at James House with Parking!
Deluxe King with Balcony - at James House with Parking!
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

6.4

Good

17 reviews

$276
Average price / night
Check Availability
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1201
Average price / night
Check Availability
Classic Queen - Curry Mansion with Heated Pool
Classic Queen - Curry Mansion with Heated Pool
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

5.0

Review score

2 reviews

$256
Average price / night
Check Availability
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1201
Average price / night
Check Availability
Deluxe King - Curry Mansion with Pool!
Deluxe King - Curry Mansion with Pool!
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

4.7

Review score

4 reviews

$269
Average price / night
Check Availability
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

8.0

Good

1 reviews

$654
Average price / night
Check Availability
Deluxe Queen at the Curry Mansion - Parking & Heated Pool!
Deluxe Queen at the Curry Mansion - Parking & Heated Pool!
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

7.2

Good

8 reviews

$288
Average price / night
Check Availability
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

10.0

Exceptional

2 reviews

$654
Average price / night
Check Availability
Classic King with Balcony at Curry Mansion
Classic King with Balcony at Curry Mansion
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

5.3

Review score

3 reviews

$276
Average price / night
Check Availability
Unique Island-Style Rooms with Custom Furniture & Art in Key West
Unique Island-Style Rooms with Custom Furniture & Art in Key West
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1258
Average price / night
Check Availability
King Suite Balcony - at James House
King Suite Balcony - at James House
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

7.6

Good

49 reviews

$264
Average price / night
Check Availability
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
Hotel
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1258
Average price / night
Check Availability
Classic King- Curry Mansion with Heated Pool!
Classic King- Curry Mansion with Heated Pool!
Hotel
Key West, FL, USA
0.3k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

4.0

Review score

2 reviews

$346
Average price / night
Check Availability
The Key West Hotel
The Key West Hotel
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

Cheap, Accommodations, Pools, Pet-friendly, 3-star, Lodgings, Places to stay, Family

10.0

Exceptional

1 reviews

$420
Average price / night
Check Availability
Ridley House - Key West Historic Inns
Ridley House - Key West Historic Inns
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Cheap, Accommodations, Pools, Inns, Pet-friendly, 3-star, Lodgings, Places to stay

8.8

Fabulous

215 reviews

$377
Average price / night
Check Availability
Blue Room at the Grand Maloney
Blue Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.3

Superb

3 reviews

$403
Average price / night
Check Availability
Yellow Room at Grand Maloney
Yellow Room at Grand Maloney
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay

5.0

Review score

1 reviews

$551
Average price / night
Check Availability
Green Room at the Grand Maloney
Green Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

8.5

Very Good

4 reviews

$429
Average price / night
Check Availability
Carriage House at Grand Maloney
Carriage House at Grand Maloney
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Places to stay

New to Booking
$403
Average price / night
Check Availability
Bunk Room at the Grand Maloney
Bunk Room at the Grand Maloney
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.7

Exceptional

3 reviews

$402
Average price / night
Check Availability
Creme Brulee Suite
Creme Brulee Suite
Hotel
Key West, FL, USA
0.4k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Parking, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay

8.1

Very Good

22 reviews

$607
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Hotels in Waterfront Playhouse.

Where to stay in Waterfront Playhouse? Best neighborhoods & areas

Waterfront Playhouse Hotels on the Map

Frequently Asked Questions

You can explore 254 verified hotels in Waterfront Playhouse. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Waterfront Playhouse vary depending on the season, location, and property type. Rates typically start from around $256 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Waterfront Playhouse include amenities such as Pool, Internet, and Security/Safety. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Waterfront Playhouse by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Waterfront Playhouse welcome pets. Currently, 22 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Waterfront Playhouse offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.