Find hotels near Waterfront Playhouse, Key West from $153

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Our top choices for Waterfront Playhouse hotels

Simonton Court Historic Inn & Cottages

2.5 star property
Historic Seaport, 0.3 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (876)
"The staff was really nice"
United States
doug
$168 nightly
The price is $190
Dec 10 - Dec 11
Total with taxes and fees
Simonton Court Historic Inn & Cottages

Almond Tree Inn Hotel - Adults Only

3.5 star property
Downtown Key West, 0.8 mi from Waterfront Playhouse
10.0 out of 10, Exceptional, (1003)
"Very nice & peaceful with a wonderful staff. Our second time staying here"
United States
Sandra
$249 nightly
The price is $280
Dec 16 - Dec 17
Total with taxes and fees
Almond Tree Inn Hotel - Adults Only

The Marquesa Hotel

3.5 star property
Historic Seaport, 0.4 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1001)
"Perfect place to stay. "
United States
Paulette
$469 nightly
The price is $528
Dec 10 - Dec 11
Total with taxes and fees
The Marquesa Hotel

The Gardens Hotel

4.0 star property
Downtown Key West, 0.6 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1001)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
$348 nightly
The price is $391
Dec 10 - Dec 11
Total with taxes and fees
The Gardens Hotel

Island City House Hotel

3.0 star property
Historic Seaport, 0.5 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (1001)
"This is the best place to stay near all the waterfront spots but still in the neighborhoods. Nice pool, ice, washer/dryer, great staff - it is so warm n friendly! Would stay again and again!"
United States
Gregory
$207 nightly
The price is $233
Dec 16 - Dec 17
Total with taxes and fees
Island City House Hotel

Orchid Key Inn - Adults Only

3.5 star property
Uptown - Upper Duval, 0.8 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1001)
"Great location and amazing staff!"
United States
Charles
$246 nightly
The price is $276
Dec 16 - Dec 17
Total with taxes and fees
Orchid Key Inn - Adults Only

The Conch House Heritage Inn

3.5 star property
Old Town Key West, 0.8 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (144)
"Amazing- I would recommend to anyone going to key west. Cozy, comfy beds, clean, and quiet. 10/10 great experience. "
United States
Savanna
$214 nightly
The price is $240
Dec 10 - Dec 11
Total with taxes and fees
The Conch House Heritage Inn

The Mermaid & Alligator

3.5 star property
Old Town Key West, 0.8 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (272)
"Property had several areas to relax."
United States
Mateo
$290 nightly
The price is $326
Dec 10 - Dec 11
Total with taxes and fees
The Mermaid & Alligator

H2O Suites - Adults Only

3.5 star property
Uptown - Upper Duval, 1 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (580)
"Great place!!"
United States
Joel
$359 nightly
The price is $404
Dec 16 - Dec 17
Total with taxes and fees
H2O Suites - Adults Only

L'Habitation Guest House

2.5 star property
Historic Seaport, 0.3 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (920)
"Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat."
United States
Robert
$136 nightly
The price is $153
Dec 14 - Dec 15
Total with taxes and fees
L'Habitation Guest House

Coco Plum Inn

3.0 star property
Downtown Key West, 0.5 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (461)
"Overall great for couple's stay. "
United States
Quazi
$179 nightly
The price is $202
Dec 16 - Dec 17
Total with taxes and fees
Coco Plum Inn

Weatherstation Inn

2.5 star property
Truman Annex, 0.3 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (992)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
$201 nightly
The price is $227
Dec 18 - Dec 19
Total with taxes and fees
Weatherstation Inn

Tropical Inn

3.5 star property
Downtown Key West, 0.7 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (363)
"The place was excellent and the service amazing "
United States
Janae
$184 nightly
The price is $204
Dec 11 - Dec 12
Total with taxes and fees
Tropical Inn

Douglas House

3.0 star property
Uptown - Upper Duval, 0.9 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (220)
"Very clean room, loved the location!"
United States
Jeffrey Ray
$167 nightly
The price is $188
Dec 15 - Dec 16
Total with taxes and fees
Douglas House

Ambrosia Key West

3.5 star property
Old Town Key West, 0.4 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1003)
"Great breakfast options, quiet, clean. Walkable where we wanted to go"
United States
Alma D
$249 nightly
The price is $280
Dec 10 - Dec 11
Total with taxes and fees
Ambrosia Key West

Ocean Key Resort - A Noble House Resort

4.0 star property
Historic Seaport, < 0.1 mi from Waterfront Playhouse
9.2 out of 10, Wonderful, (1009)
"Great stay."
United States
Sarit
$463 nightly
The price is $521
Dec 17 - Dec 18
Total with taxes and fees
Ocean Key Resort - A Noble House Resort

Marrero's Guest Mansion

3.5 star property
Downtown Key West, 0.4 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (335)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
$325 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Marrero's Guest Mansion

Duval House

3.0 star property
Downtown Key West, 0.7 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1002)
"Had a great stay"
United States
Bren Albert
$150 nightly
The price is $166
Dec 10 - Dec 11
Total with taxes and fees
Duval House

Westwinds Inn

3.5 star property
Historic Seaport, 0.6 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1003)
"Staff was amazing Room super clean"
United States
JULIE
$210 nightly
The price is $236
Dec 10 - Dec 11
Total with taxes and fees
Westwinds Inn

The Grand Guesthouse

2.5 star property
Old Town Key West, 1 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (1001)
"Great stay"
United States
Ginger
$216 nightly
The price is $242
Dec 10 - Dec 11
Total with taxes and fees
The Grand Guesthouse
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.

Top Waterfront Playhouse Hotel Reviews

Hotels near other Waterfront Playhouse attractions

Frequently asked questions

What are the top-rated hotels near Waterfront Playhouse?
Discover the top-rated hotels near Waterfront Playhouse that offer a delightful mix of comfort and charm for your stay in Key West.

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel is a welcoming 3.5-star retreat situated just an 18-minute walk from Waterfront Playhouse, with an impressive review rating of 10. This adults-only oasis features an outdoor pool, hot tub, and terraces for relaxing afternoons. Guests can enjoy complimentary breakfast daily, along with premium Egyptian cotton sheets and a peaceful garden atmosphere. The hotel also offers convenient amenities like electric car charging stations and easy access to nearby beaches and water activities.

The Gardens Hotel

The Gardens Hotel is a charming 4-star hotel located only 12 minutes on foot from Waterfront Playhouse, with a stellar review rating of 9.8. Guests can unwind in beautifully landscaped gardens or take a dip in the inviting outdoor pool. The hotel offers a delicious complimentary breakfast and unique amenities such as in-room kitchens and massage services. Visitors will appreciate the nearby local attractions, as well as the serene ambiance that makes this hotel a perfect getaway.

Orchid Key Inn - Adults Only

Orchid Key Inn is a stylish 3.5-star hotel just 17 minutes from Waterfront Playhouse, with a remarkable review rating of 9.8. This adults-only hotel features an outdoor pool and a private hot tub, creating an ideal environment for relaxation. Guests can indulge in free daily breakfast and explore nearby beaches and water sports, including snorkeling and kayaking. With its elegant design and attention to detail, Orchid Key Inn promises a memorable stay in the heart of Key West.
What hotels are within walking distance to Waterfront Playhouse?
For a delightful stay near Waterfront Playhouse, Key West offers a selection of top-rated hotels that provide both comfort and convenience.

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only is a charming 3.5-star hotel located just an 18-minute walk from Waterfront Playhouse, with an impressive review rating of 10. This adults-only oasis features an outdoor pool, hot tub, and a beautiful terrace for travelers to unwind. With amenities like free breakfast, poolside bar, and luxurious Egyptian cotton sheets, it ensures a relaxing stay in the heart of Key West.

The Gardens Hotel

The Gardens Hotel is a serene 4-star retreat located only 12 minutes from Waterfront Playhouse, rated highly with a review rating of 9.8. Guests can enjoy a picturesque outdoor pool and beautiful gardens during their stay. The hotel offers complimentary breakfast, a restaurant with garden views, and unique amenities like in-room massage services and yoga classes, making it a perfect choice for relaxation and rejuvenation.

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only is a stylish 3.5-star hotel situated just 17 minutes from Waterfront Playhouse, with an outstanding review rating of 9.8. This adults-only hotel features an outdoor pool and a hot tub, along with complimentary breakfast and designer toiletries for an indulgent experience. Guests can take advantage of nearby kayaking, snorkeling, and boat tours, making it an excellent base for exploring the vibrant waters of Key West.
How much is a hotel near Waterfront Playhouse?
Staying near Waterfront Playhouse is a treat, with plenty of hotels from $153 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Waterfront Playhouse?
For families seeking a memorable stay near Waterfront Playhouse, these top-rated hotels in Key West offer a variety of family-friendly amenities and activities.

Margaritaville Beach House Key West

Located just 3.1 miles from Waterfront Playhouse, Margaritaville Beach House Key West is a delightful 4-star hotel with a review rating of 8.8. This family-friendly haven features a sparkling outdoor pool, a kitchenette in each room, and toys for children to enjoy. Guests can also unwind in their cozy rooms equipped with mini-refrigerators and daily housekeeping, ensuring a comfortable stay.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West is a charming 4-star hotel located 3.8 miles from Waterfront Playhouse, a review rating of 7.8. Families will appreciate the accessible pool and connecting rooms, making it easy to accommodate everyone. Additional amenities include a game room, daily breakfast for children, and a lovely garden area for relaxation.

Hyatt Centric Key West Resort and Spa

Just a 5-minute walk from Waterfront Playhouse, Hyatt Centric Key West Resort and Spa offers a luxurious stay with a great traveler rating score of 9.0 and a 4-star rating. This family-friendly hotel features a beautiful pool and kid-friendly restaurant meals. Guests can enjoy premium bedding, beach access, and a range of wellness options, including an on-site spa and various water sports activities.
Which hotels near Waterfront Playhouse offer the best views?
Discover stunning hotels near Waterfront Playhouse that offer breathtaking views and exceptional experiences for every traveler.

The Gardens Hotel

The Gardens Hotel, rated an impressive 9.8 by travelers, is a charming 4-star hotel located just a 12-minute walk from Waterfront Playhouse. This oasis features lush gardens and a serene atmosphere, perfect for relaxation. Guests can enjoy complimentary breakfast, a beautiful outdoor pool, and in-room massages. The garden view restaurant adds to the tranquil ambiance, making it a perfect escape in Key West.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa is a 4-star hotel rated 9.0 by travelers, located just a 5-minute walk from Waterfront Playhouse. This resort features a stunning partial ocean view and a full-service spa with unique treatments, including deep tissue massages. Guests can unwind by the outdoor pool or enjoy a meal at the oceanview restaurant. The convenient location near the beach and activities like windsurfing and kayaking enhances the overall experience.

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton boasts a review rating of 8.4 and is situated 1.7 miles from Waterfront Playhouse. This 4-star hotel offers gorgeous ocean views and is set on a private beach. Travelers can take advantage of amenities like onsite sailing and a full-service spa. The outdoor pools and beach bar provide perfect spots to relax while soaking in the sun and scenery.
What are the best affordable hotels near Waterfront Playhouse?
Finding the perfect and affordable stay near Waterfront Playhouse is easy with these top-rated options that cater to every traveler's needs.

The Grand Guesthouse

The Grand Guesthouse is situated just 1.6 miles from Waterfront Playhouse, with a traveler review rating of 9.6. This quaint travelerhouse provides free continental breakfast and convenient free parking nearby, making it ideal for budget-conscious travelers. With amenities such as a kitchenette and access to local windsurfing, travelers can enjoy both comfort and adventure during their stay.

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages offers travelers a charming stay just an 8-minute walk from Waterfront Playhouse. With an impressive review rating of 9.8, this hotel features delightful amenities including free continental breakfast and an outdoor pool. Travelers can also enjoy nearby kayaking and boat tours, making it a great choice for those looking to explore the local waters while enjoying comfortable accommodations.

LA TE DA Hotel - Adults Only

LA TE DA Hotel - Adults Only is a relaxing retreat located 20 minutes from Waterfront Playhouse, with a perfect review rating of 9.8. Designed exclusively for adults, this hotel offers a serene atmosphere complemented by an outdoor pool and nearby boating activities. Guests can unwind on the terrace or take advantage of the free WiFi during their stay, ensuring a comfortable and rejuvenating experience.
What are the best boutique hotels near Waterfront Playhouse?
Discover the charm of boutique hotels near Waterfront Playhouse, perfect for travelers seeking unique stays in Key West.

Artist House Key West

Situated just an 8-minute walk from Waterfront Playhouse, Artist House Key West is a delightful 3.5-star boutique hotel with a stellar review rating of 9.8. Guests will enjoy a complimentary breakfast each morning and can unwind in the hot tub or explore nearby windsurfing and kayaking. The hotel also features a beautiful garden and cozy balconies, making it an ideal spot for relaxation after a day of adventure.

Weatherstation Inn

Only 6 minutes on foot from Waterfront Playhouse, Weatherstation Inn boasts a remarkable 9.4 review rating. This boutique hotel offers an inviting outdoor pool, complimentary breakfast, and easy access to local snorkeling and kayaking tours. Guests appreciate the historical charm of the inn, complete with a terrace for enjoying the warm Key West evenings.

The Inn on Fleming

The Inn on Fleming is a quaint 3.5-star boutique hotel located 18 minutes from Waterfront Playhouse, earning an impressive review rating of 9.4. Guests can indulge in free daily breakfast, relax by the outdoor pool, or take part in nearby boat tours and snorkeling adventures. The hotel features beautiful terraces and premium bedding, ensuring a comfortable and memorable stay.
Are there any hotels with pools close to Waterfront Playhouse?
Finding a perfect hotel with a pool near the Waterfront Playhouse can enhance your Key West experience. Dive into these top-rated options that cater to your comfort and leisure needs.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West is a delightful 4-star hotel located just 3.8 miles from the Waterfront Playhouse, a review rating of 7.8. This resort features an accessible outdoor pool with sun loungers and poolside bar, perfect for relaxing under the sun. Guests can also enjoy amenities like free onsite parking, an arcade game room, and complimentary beach towels, making it an excellent choice for families and leisure travelers.

Pier House Resort & Spa

Pier House Resort & Spa is a luxurious 4-star hotel located just a 2-minute walk from the Waterfront Playhouse, with an impressive review rating of 9.0. It features an accessible outdoor pool with sun loungers and a poolside bar, offering a perfect spot to unwind. Guests can also take advantage of amenities like a beachfront restaurant, a full-service spa, and complimentary beach towels, making it an ideal choice for travelers seeking relaxation and convenience.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses, situated only 1.1 miles from the Waterfront Playhouse, offers a fantastic stay with a review rating of 8.6. This 4-star hotel features a beautiful outdoor pool complete with sun loungers and a poolside bar, ideal for a refreshing dip. Guests can indulge in additional amenities such as beachfront access, a full-service spa, and complimentary beach towels, ensuring a comfortable and enjoyable stay.
What are the best pet-friendly hotels near Waterfront Playhouse?
For travelers seeking pet-friendly accommodations near Waterfront Playhouse, these top-rated hotels in Key West offer the perfect blend of comfort and amenities for you and your furry friend.

The Gardens Hotel

The Gardens Hotel is a 4-star oasis just a 12-minute walk from Waterfront Playhouse, with an impressive review rating of 9.8. This hotel welcomes pets with essential amenities such as food and water bowls, making it a great choice for pet owners. Guests can enjoy the beautiful outdoor pool, complimentary breakfast, and a relaxing terrace. With nearby kayaking and windsurfing options, your stay will be both comfortable and adventurous.

Artist House Key West

Located only 8 minutes from Waterfront Playhouse, Artist House Key West is a charming 3.5-star hotel with a stellar review rating of 9.8. This pet-friendly hotel offers food and water bowls for your four-legged companions. Guests can indulge in a free buffet breakfast, unwind in the hot tub, and explore nearby snorkeling or kayaking activities. Its inviting garden and cozy atmosphere ensure a delightful stay for both you and your pet.

The Garden House

Just a 10-minute stroll from Waterfront Playhouse, The Garden House is a cozy 3-star hotel with an excellent review rating of 9.2. This pet-friendly hotel provides food and water bowls for your furry friend and features an outdoor pool and a lovely terrace. Guests appreciate the convenience of onsite parking and daily breakfast options, enhancing the overall experience. The hotel's location allows easy access to nearby beaches and shopping areas.
Can I book a fully refundable hotel close to Waterfront Playhouse?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Waterfront Playhouse", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.
Can I find Expedia discounts for hotels near Waterfront Playhouse?
To look for discounts on hotels near Waterfront Playhouse, join One Key™—our free travel rewards program. One Key members always get our best prices and earn OneKeyCash™* on eligible bookings for every dollar spent. Another way to save is by bundling your hotel and flights together on Expedia.

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