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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Waterfront Playhouse hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
A swimming pool with lounge chairs, surrounded by palm trees and greenery.
A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 1.3 km from Waterfront Playhouse
United States
Teresa
Rp4.304.586
Rp4.842.659 total
includes taxes & fees
25 Oct - 26 Oct
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.
A large, two-story building with a balcony, surrounded by dense tropical foliage.
A wooden deck with lush greenery and a pool area.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
Maricela
Rp2.831.792
Rp3.504.342 total
includes taxes & fees
27 Oct - 28 Oct
Douglas House - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.
A patio with a white wicker lounge chair, a wooden table with a book and a potted plant, surrounded by lush tropical foliage and palm trees.
A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.
A hotel room with a large bed, a nightstand, a desk, a bathroom with a shower, and a painting of a pier over water on the wall.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
Rp4.358.541
Rp4.903.358 total
includes taxes & fees
28 Oct - 29 Oct
Orchid Key Inn - Adults Only
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.
A bar area with a counter, chairs, and a clock.
A colonial-style building with a porch, surrounded by lush tropical vegetation.

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
Rp6.456.879
Rp7.263.989 total
includes taxes & fees
26 Oct - 27 Oct
The Gardens Hotel
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
A pathway flanked by lush green foliage leading to a gated entrance.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.

5. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Wayne
Rp2.680.808
Rp3.015.909 total
includes taxes & fees
27 Oct - 28 Oct
Simonton Court Historic Inn & Cottages
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A pool area with lounge chairs and a wooden building with balconies.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A garden with a pond, rocks, and various plants.

6. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
Rp3.568.893
Rp4.015.005 total
includes taxes & fees
26 Oct - 27 Oct
Island City House Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.
A two-story building with a white picket fence, a mailbox, and a small tree in front.

7. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
Rp2.508.394
Rp3.209.932 total
includes taxes & fees
26 Oct - 27 Oct
Duval House
A two-story house with a covered porch, a brick pathway, and a large tree.
A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Josh
Rp7.741.734
Rp9.724.628 total
includes taxes & fees
26 Oct - 27 Oct
The Marquesa Hotel
A pool area with lounge chairs and palm trees.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

9. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
Rp5.379.608
Rp7.266.519 total
includes taxes & fees
27 Oct - 28 Oct
Santa Maria Suites
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.

10. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
Rp2.923.452
Rp3.288.884 total
includes taxes & fees
25 Oct - 26 Oct
Westwinds Inn
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.
A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.

11. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Robert
Rp3.580.408
Rp4.027.959 total
includes taxes & fees
25 Oct - 26 Oct
Weatherstation Inn
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.
A large, two-story house with a prominent tower and a covered porch.
A grand staircase with ornate railings and a chandelier.

12. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
Rp3.222.367
Rp5.902.276 total
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A gated entrance with lush green foliage and a white picket fence.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.
A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

13. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
Rp3.613.892
Rp4.065.583 total
includes taxes & fees
25 Oct - 26 Oct
Coco Plum Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
A hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.
A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
A spacious living room with a high ceiling, a ceiling fan, a large painting, a sofa, a coffee table, and a dining area with a table and chairs.

14. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
Rp3.914.160
Rp4.403.431 total
includes taxes & fees
25 Oct - 26 Oct
Ambrosia Key West
A green house with a white porch, a flag, and a sign advertising a property for sale.
A bathroom with a vanity, a mirror, and a window with blinds.
A room with a ceiling fan, an air conditioning unit, a window with blinds, a sofa with patterned cushions, a small round table, and a floor lamp.
A bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.

15. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Michael
Rp3.060.439
Rp3.443.129 total
includes taxes & fees
28 Oct - 29 Oct
L'Habitation Guest House - Adults Only
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.

16. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
Rp1.603.087
Rp3.018.158 total
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A yellow building with a door marked '7'.
A garden with a stone pathway, a wooden fence, and various tropical plants.
A pool area with a circular pool, lounge chairs, and a gazebo.

17. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
Rp5.813.215
Rp6.540.092 total
includes taxes & fees
25 Oct - 26 Oct
Alexander Palms Court
A covered porch with white railings, wooden benches, and a hanging light fixture.
A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.
A sign for Marrero's Guest Mansion in Key West, FL, by Verdigris Hotels.
A pool area with lounge chairs and a small palm tree.

18. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, 0.6 km from Waterfront Playhouse
United States
Michael
Rp5.829.408
Rp6.558.084 total
includes taxes & fees
25 Oct - 26 Oct
Marrero's Guest Mansion
A poolside area with lounge chairs, umbrellas, and a pergola.
A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

19. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West, 1.1 km from Waterfront Playhouse
United States
Lisa and David
Rp4.498.000
Rp5.971.185 total
includes taxes & fees
27 Oct - 28 Oct
Ella's Cottages - Key West Historic Inns
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A covered outdoor area with a pool, palm trees, and lounge chairs.
A tropical setting with palm trees and a building with a white facade and dark roof.

20. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.6 km from Waterfront Playhouse
United States
Dana Nicole
Rp3.261.950
Rp4.803.190 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
View all properties

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,003 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
564 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,001 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,000 reviews
View
A modern interior with a staircase, a sofa set, a wooden table, and a television.
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,007 reviews
View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A balcony with a table set for breakfast, overlooking the sea.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
Rp5.379.608
Rp7.509.410 total
includes taxes & fees
27 Oct - 28 Oct
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A resort with a beach, a dock, and a water view.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A balcony with a view of the ocean, a sofa, and a massage table.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
Rp3.270.406
Rp4.934.148 total
includes taxes & fees
25 Oct - 26 Oct
Pier House Resort & Spa
A white building with green shutters and a white picket fence.
A pool area with lounge chairs, a small table, and a thatched umbrella.
A brick pathway leading to a green door, surrounded by lush tropical plants and a white fence.
A modern kitchen with white cabinetry, a central island, and a view of the outdoors.

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Key West Historic District
Rp3.598.400
Rp4.959.135 total
includes taxes & fees
25 Oct - 26 Oct
Ridley House - Key West Historic Inns
A hotel with a swimming pool, balconies, and a view of the sea.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A balcony with a view of the ocean, a table, chairs, and a railing.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
Rp4.210.128
Rp6.052.149 total
includes taxes & fees
25 Oct - 26 Oct
Hyatt Centric Key West Resort and Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A covered outdoor area with a pool, palm trees, and lounge chairs.
A tropical setting with palm trees and a building with a white facade and dark roof.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
Rp3.261.950
Rp4.803.190 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
A poolside area with lounge chairs, umbrellas, and a pergola.
A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West
Rp4.498.000
Rp5.971.185 total
includes taxes & fees
27 Oct - 28 Oct
Ella's Cottages - Key West Historic Inns
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.
A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.
A table with chairs in a lush indoor garden setting.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Rp3.598.400
Rp4.959.135 total
includes taxes & fees
27 Oct - 28 Oct
Lighthouse Hotel - Key West Historic Inns
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A pool area with lounge chairs and a wooden building with balconies.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A garden with a pond, rocks, and various plants.

Island City House Hotel

Island City House Hotel
Key West Historic District
Rp3.568.893
Rp4.015.005 total
includes taxes & fees
26 Oct - 27 Oct
Island City House Hotel

Top Waterfront Playhouse Hotel Reviews

Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Location, Everything within walking distance"
Constance 2-night trip
Posted 14 hours ago
Weatherstation Inn
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Close to everything!!"
David S 5-night trip
Posted 15 hours ago
Pier House Resort & Spa
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"We had no issues. Room clean, restaurant good!"
Michael 4-night trip
Posted 1 day ago
Opal Key Resort & Marina, Key West
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Great location and the ocean facing suite was amazing and very clean. Staff was super friendly. We really enjoyed the in-room breakfast offering as well. The pool in particular was great for an afternoon dip and to watch the sunset. We would absolutely come back!"
Martine 5-night trip
Posted 1 day ago
Ocean Key Resort - A Noble House Resort
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"The property manager was very helpful and the breakfast organizer (Sonya) provided the very best display and variety of food with warm greeting."
Carolyn 4-night trip
Posted 3 days ago
Ridley House - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The property was wonderfully located, clean, and beautiful. Highly recommend."
Lance 3-night trip
Posted 4 days ago
Heron House - Adult Only
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 5 days ago
La Concha Key West, Autograph Collection
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"Had an excellent time. Absolutely beautiful hotel and amazing staff!"
Kertpal 1-night trip
Posted 13 days ago
Hyatt Vacation Club at Sunset Harbor, Key West
Ocean Key Resort & Spa

Ocean Key Resort & Spa

10/10 Excellent
"This resort was amazing! The best area and most beautiful in Old Town. Craig and the whole staff were lovely! Would def return!"
Lola 1-night trip
Posted 2 months ago
Ocean Key Resort & Spa

Other attractions near Waterfront Playhouse

A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 reviews)
This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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A large cruise ship docked at a pier with palm trees and a clear sky.

Mallory Dock

8.8/10 (1,152 reviews)
You can find the perfect gifts to bring home at Mallory Dock during your trip to Key West. Wander the area's seaside or simply enjoy one of its lively bars.
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A red brick building with arched windows and a clock on the facade.

Museum of Art & History at the Custom House

8.4/10 (15 reviews)
You can spend time studying the exhibits at Museum of Art & History at the Custom House during your trip to Key West. Discover the area's lively bars and its lively festivals.
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A two-story house with green shutters and a wooden balcony.

Audubon House and Tropical Gardens

8.8/10 (378 reviews)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
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A historic building with maritime museum banners, a rusty boat, and a tree-lined street.

Mel Fisher Maritime Museum

9.2/10 (56 reviews)
Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.
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Roy John-Karl Gallery

You can spend time browsing the exhibits at Roy John-Karl Gallery in Key West. Stroll along the area's seaside or simply savour its lively bars.
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Sloppy Joe's Bar

Sloppy Joe's Bar is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Experience the area's great live music and entertainment choices.
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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, take a look at the 1400 hotels and other accommodation options you'll find within a mile.
Where is the best place to stay near Waterfront Playhouse?
Adjacent to Waterfront Playhouse, Pier House Resort & Spa is one of the top choices for your stay based on our traveller data, and this resort offers a full-service spa and a private beach. Other good options within a short distance include Hyatt Centric Key West Resort and Spa and Opal Key Resort & Marina, Key West.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1400 hotels and other accommodation options 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 room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to view the best deals near Waterfront Playhouse.
What can I see and do near Waterfront Playhouse?
Harry S. Truman Little White House, Florida Keys Eco - Discovery Center and Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Key West Lighthouse and Keeper's Quarters Museum, Fort Zachary Taylor Historic State Park and Fort East Martello Museum and Gallery are landmarks to visit in the area. You can watch performances at Red Barn Theater, Key West Film Society and The Key West Theater if you're interested in local theatre.