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Hotels with Pools in Key West

Find the hotels with pools that appeal to you the most

The best hotels with pools in Key West

Check out our pick of great hotels with pools in Key West

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Southernmost Point Guest House & Garden Bar

Downtown Key West, Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach.

A
Alex
From
France
Beautiful historic property in perfect location. Rooms were well appointed and very clean. Staff were friendly and helpful. A wonderful place to stay.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,174 reviews
Price from
US$481.85
1 night, 2 adults
Check availability

Douglas House

Downtown Key West, Key West

Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available.

V
Vladlen
From
Australia
Great location, only few minutes to Southernmost Point of the Continental U.S.A. Mallory Square is about 20 min walk along Duval St, where most of restaurant are. Staff at the Douglas House were exceptional, Jose is very friendly and helpful.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 2,564 reviews
Price from
US$206.10
1 night, 2 adults
Check availability

Simonton Court Historic Inn & Cottages

Downtown Key West, Key West

Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access.

j
john
From
Ireland
Exceptional experience, upgraded to a cottage on arrival.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,052 reviews
Price from
US$279
1 night, 2 adults
Check availability

Weatherstation Inn Circa 1911

Downtown Key West, Key West

Set within 500 metres of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...

B
BURAK
From
Turkey
The location is fantastic! In a quiet and secure neighborhood, surrounded by trees and adjacent to the ocean. We wished if we stayed more.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 262 reviews
Price from
US$199
1 night, 2 adults
Check availability

H2O Suites- Adults Only

Downtown Key West, Key West

This adult-only Key West H2O Suites is 200 metres from Duval Street and features a year-round outdoor rooftop pool with a sun terrace. Guests can enjoy the on-site bar.

d
denis
From
France
Best hotel during our Florida road trip . The place is quiet , the room was excellent, the staff so friendly and welcoming . Champagne or / and cocktail to welcome you , nice gift for our departure. Pick a room with a swimming pool or a deluxe suite . So nice to have the pool in the room . The rooftop pool is very nice too as the bartender .
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 488 reviews
Price from
US$299
1 night, 2 adults
Check availability

Island City House

Hotel in Downtown Key West, Key West

Offering an outdoor pool, this historic Key West Island City House hotel is 2 minutes’ walk from the Key West sea port. Features include free WiFi, garden, and rooms with a kitchen.

R
RONALD
From
United States
Full apartment with well kept antique furnishings. Beautiful grounds. In the heart of Key West. Walking distance to just about everywhere that you’d want to do on the island.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 713 reviews
Price from
US$313.60
1 night, 2 adults
Check availability

The Mermaid & The Alligator

Hotel in Downtown Key West, Key West

Boasting an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is situated in the centre of Key West, less than 1 km from South Beach.

M
Marius
From
Netherlands
The room was designed with a lot of love and really gave a cozy island vibe. We felt comfortable from the first second. The breakfast was great. The location super convenient, with enough parking. And the staff was very welcoming and helpful.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 147 reviews
Price from
US$284.20
1 night, 2 adults
Check availability

Hyatt Vacation Club at Windward Pointe

Hotel in Key West

This Hyatt Windward Pointe is situated in Key West, 5.7 km from the Southernmost Point, and boasts a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.

M
Mateja
From
Slovenia
Location is great, a bit outside the center, near sea. Staff was nice and helpfull. The room was clean, big, with extra big balcony. Beds were clean and comftorable. Apartment was very spacefull, kitchen has a lot of equipment. Whole place is very clean. Pool is great and also all the place around it. Parking space.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 894 reviews
Price from
US$256.90
1 night, 2 adults
Check availability

Key West Villas

Downtown Key West, Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

a
anne
From
Switzerland
If I could give more than 10 I would! Everything was perfect: the location (in the heart of Key West, parking space available), the rooms (they’re even nicer as on the homepage), the poolside.. everything was so tasteful and clean. And of course the hosts ! They make everything to make you feel home. Snacks and drinks available all day long, happy hour every day and the bottle of wine offered upon arrival!! We just can strongly recommend this lovely place.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 322 reviews
Price from
US$549
1 night, 2 adults
Check availability

Orchid Key Inn - Adults Only

Hotel in Downtown Key West, Key West

This historic Key West Orchid Key Inn - Adults Only is on Duval Street 3 minutes’ walk from the Ernest Hemingway House and Museum.

E
Erwin
From
Germany
Exceptionally beautiful little hotel complex right on Duval Street, not far from the most interesting sights. However, in the summer heat, even short distances on foot become an ordeal. It is advisable to rent a scooter from the rental station right next door. Rooms are very clean, well-kept furnishings in a high-class style. The staff are very, very friendly and happy to help with any problem. For a hotel that does not have its own kitchen/restaurant, the breakfast is excellent and leaves little to be desired other than hot food. As we said when we left: if we ever return to Key West, we will stay here!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 301 reviews
Price from
US$241.40
1 night, 2 adults
Check availability
All hotels with pools in Key West

Top picks for Key West hotels

Explore our most popular hotels in Key West

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Show hotels on map

Filter by:

Review score

Southernmost Point Guest House & Garden Bar

Downtown Key West, Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach.

A
Alex
From
France
Beautiful historic property in perfect location. Rooms were well appointed and very clean. Staff were friendly and helpful. A wonderful place to stay.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,174 reviews
Price from
US$481.85
1 night, 2 adults
Check availability

Douglas House

Downtown Key West, Key West

Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available.

V
Vladlen
From
Australia
Great location, only few minutes to Southernmost Point of the Continental U.S.A. Mallory Square is about 20 min walk along Duval St, where most of restaurant are. Staff at the Douglas House were exceptional, Jose is very friendly and helpful.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 2,564 reviews
Price from
US$206.10
1 night, 2 adults
Check availability

Simonton Court Historic Inn & Cottages

Downtown Key West, Key West

Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access.

j
john
From
Ireland
Exceptional experience, upgraded to a cottage on arrival.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,052 reviews
Price from
US$279
1 night, 2 adults
Check availability

Weatherstation Inn Circa 1911

Downtown Key West, Key West

Set within 500 metres of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...

B
BURAK
From
Turkey
The location is fantastic! In a quiet and secure neighborhood, surrounded by trees and adjacent to the ocean. We wished if we stayed more.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 262 reviews
Price from
US$199
1 night, 2 adults
Check availability

H2O Suites- Adults Only

Downtown Key West, Key West

This adult-only Key West H2O Suites is 200 metres from Duval Street and features a year-round outdoor rooftop pool with a sun terrace. Guests can enjoy the on-site bar.

d
denis
From
France
Best hotel during our Florida road trip . The place is quiet , the room was excellent, the staff so friendly and welcoming . Champagne or / and cocktail to welcome you , nice gift for our departure. Pick a room with a swimming pool or a deluxe suite . So nice to have the pool in the room . The rooftop pool is very nice too as the bartender .
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 488 reviews
Price from
US$299
1 night, 2 adults
Check availability

Island City House

Hotel in Downtown Key West, Key West

Offering an outdoor pool, this historic Key West Island City House hotel is 2 minutes’ walk from the Key West sea port. Features include free WiFi, garden, and rooms with a kitchen.

R
RONALD
From
United States
Full apartment with well kept antique furnishings. Beautiful grounds. In the heart of Key West. Walking distance to just about everywhere that you’d want to do on the island.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 713 reviews
Price from
US$313.60
1 night, 2 adults
Check availability

The Mermaid & The Alligator

Hotel in Downtown Key West, Key West

Boasting an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is situated in the centre of Key West, less than 1 km from South Beach.

M
Marius
From
Netherlands
The room was designed with a lot of love and really gave a cozy island vibe. We felt comfortable from the first second. The breakfast was great. The location super convenient, with enough parking. And the staff was very welcoming and helpful.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 147 reviews
Price from
US$284.20
1 night, 2 adults
Check availability

Hyatt Vacation Club at Windward Pointe

Hotel in Key West

This Hyatt Windward Pointe is situated in Key West, 5.7 km from the Southernmost Point, and boasts a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.

M
Mateja
From
Slovenia
Location is great, a bit outside the center, near sea. Staff was nice and helpfull. The room was clean, big, with extra big balcony. Beds were clean and comftorable. Apartment was very spacefull, kitchen has a lot of equipment. Whole place is very clean. Pool is great and also all the place around it. Parking space.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 894 reviews
Price from
US$256.90
1 night, 2 adults
Check availability

Key West Villas

Downtown Key West, Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

a
anne
From
Switzerland
If I could give more than 10 I would! Everything was perfect: the location (in the heart of Key West, parking space available), the rooms (they’re even nicer as on the homepage), the poolside.. everything was so tasteful and clean. And of course the hosts ! They make everything to make you feel home. Snacks and drinks available all day long, happy hour every day and the bottle of wine offered upon arrival!! We just can strongly recommend this lovely place.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 322 reviews
Price from
US$549
1 night, 2 adults
Check availability

Orchid Key Inn - Adults Only

Hotel in Downtown Key West, Key West

This historic Key West Orchid Key Inn - Adults Only is on Duval Street 3 minutes’ walk from the Ernest Hemingway House and Museum.

E
Erwin
From
Germany
Exceptionally beautiful little hotel complex right on Duval Street, not far from the most interesting sights. However, in the summer heat, even short distances on foot become an ordeal. It is advisable to rent a scooter from the rental station right next door. Rooms are very clean, well-kept furnishings in a high-class style. The staff are very, very friendly and happy to help with any problem. For a hotel that does not have its own kitchen/restaurant, the breakfast is excellent and leaves little to be desired other than hot food. As we said when we left: if we ever return to Key West, we will stay here!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 301 reviews
Price from
US$241.40
1 night, 2 adults
Check availability
All hotels with pools in Key West

Looking for a hotel with pools?

‘Does it have a pool?’ is arguably one of the most common questions when booking a stay in any location. These hotels offer a great way to keep active during your holiday without having to hit the gym. Indoor pools allow you to practice your backstroke come rain or shine, whereas outdoor options allow you to relax on a sun lounger after swimming a few lengths.

Most booked hotels with pools in Key West and surroundings in the past month

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Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 3,500 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 1,614 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,936 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 2,343 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 3,442 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2,873 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 1,002 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 1,839 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 1,375 reviews

Popular with guests booking hotels with pools in Key West

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 1,167 reviews

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 632 reviews

Lighthouse Hotel is located in the heart of iconic Key West, opposite the Ernest Hemingway Home and Museum and the Keeper's Quarters Museum.

From US$612 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 3,500 reviews

This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. South Beach - Key West is 0.5 miles away from the property.

From US$358.73 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 705 reviews

Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles.

From US$550.23 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 30 reviews

This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.

From US$388.80 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 204 reviews

Offering a heated outdoor pool, this boutique Ella's Cottages is located in Old Town Key West 2 minutes' walk from Duval Street. Free WiFi and a poolside continental breakfast are provided.

From US$649.13 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,268 reviews

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.

From US$370.13 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 892 reviews

Offering an outdoor pool, Duval Inn is located in Key West. Free WiFi access is available. This Key West bed and breakfast includes both an indoor and outdoor seating area as well as a refrigerator.

From US$386.61 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 1,245 reviews

Located in Key West, Florida, Winslow's Bungalows features 3 swimming pools, free WiFi access, and complimentary continental breakfast.

From US$583.88 per night

Save money on pools in Key West and nearby – budget options available

Offering free WiFi and sea views, Lighthouse Suites Collection is an accommodation set in the heart of Key West, just 600 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2,873 reviews

Located one block from the Ernest Hemingway House and Museum in Key West, Florida, this guesthouse offers a large tropical garden and an outdoor pool. Rooms feature free Wi-Fi.

From US$426.38 per night

Set in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub offers free WiFi, a garden and air...

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 18 reviews

Old Town Garden Villas - Andros Suite has a patio and is located in Key West, within just 400 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 152 reviews

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Old Town Garden Villas - Abaco Suite has a patio and is located in Key West, within just 500 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 14 reviews

Boasting air-conditioned accommodation with a terrace, Casa Havana @ Duval Square R22 is situated in Key West. Guests can benefit from a balcony and an outdoor pool.

Located in Key West, 500 metres from Ernest Hemingway Home and Museum and 600 metres from Duval Street, Sea Esta Suite - Duval Square provides accommodation with amenities such as free WiFi and a TV.

From US$1,591.66 per night

Great access to the city centre. Check these hotels with pools in Key West and nearby

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 3 reviews

Offering free WiFi and sea views, Key West Light Suite is an accommodation situated right in the heart of Key West, just 700 metres from South Beach and 200 metres from Ernest Hemingway Home and...

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 524 reviews

Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi.

From US$309.38 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 16 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Casa Key West-Pool & Free Parking offers free WiFi, air conditioning and household...

From US$1,627.93 per night
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 2 reviews

Set in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!

From US$1,033.20 per night
Scored out of 10, guest rating 5.5
Passable - What previous guests thought, 2 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Coconut Palm offers free WiFi, air conditioning and household amenities such as a...

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 6 reviews

Set in the centre of Key West, 300 metres from South Beach and 400 metres from Southernmost Point, Keys Please! offers free WiFi, a garden and air conditioning.

From US$1,895.96 per night
Scored out of 10, guest rating 4.5
Disappointing - What previous guests thought, 2 reviews

Situated in the centre of Key West, 300 metres from Fort Zachary Taylor State Park Beach and 400 metres from Ernest Hemingway Home and Museum, Leo's Lodge offers free WiFi, massage services and air...

From US$678.89 per night

Set in the centre of Key West, 300 metres from Fort Zachary Taylor State Park Beach and 400 metres from Ernest Hemingway Home and Museum, Chagall's Corner offers free WiFi, massage services and air...

From US$678.89 per night

FAQ about hotels with pools in Key West

Hotels with a pool that guests love in Key West

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The Laureate Key West

Hotel with Pools in Key West
Avg. price/night: US$319.50
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,000 reviews
Swimming pool was great and had all attractions around it to play – kids loved it!!!
Guest review by
epn4515
Family with young children

Simonton Court Historic Inn & Cottages

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$482.63
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,052 reviews
Extraordinary place with four swimming pools and wonderful atmosphere
Guest review by
Adrian
Young couple

Southwinds Motel

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$316.38
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 1,927 reviews
Loved the rooms and really nice swimming pools.
Guest review by
Clare
Young couple

Nyah - Adult Exclusive

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$372.03
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,715 reviews
Swimming pool , close to the city centre
Guest review by
Darwin
Solo traveller

Wicker Guesthouse

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$426.38
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2,873 reviews
loved the quirkiness of this place, right in the centre of the night life district although a quiet room great for night life and restaurants. Staff super friendly and breakfast was very good. Court yard swimming pool a bonus all the rooms are different and non corporate typical Key West Flair.
Guest review by
Adrian
Solo traveller

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Hotel with Pools in Key West
Avg. price/night: US$306
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 1,839 reviews
Location Parking Shuttle bus Swimming pool
Guest review by
Alusine
Family with young children

Parrot Key Hotel & Villas

Hotel with Pools in Key West
Avg. price/night: US$352.86
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 3,310 reviews
Very nice hotel with a good outdoor swimming pool.
Guest review by
Łukasz
Young couple

The Cabana Inn Key West - Adult Exclusive

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$358.86
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 838 reviews
Great location right in the heart of the key west! HUGE room, with a great big comfy bed Facilities phenomenal, complimentary happy hour with wine / cheese / snacks was a lovely touch, great breakfast in the morning! Even with the local cockerel! Swimming pool and hot tub open 24hrs was amazing with towels provided next to pool. Parking easy and simple, allowed us to stay a couple of hours after check out too which helped us loads before we left Staff were amazing, really friendly man at check in who helped us!
Guest review by
Craig
Young couple

Nyah - Adult Exclusive

Hotel with Pools in Downtown Key West, Key West
Avg. price/night: US$372.03
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,715 reviews
The hot tube , the swimming pools and the breath fast.
Guest review by
Gabriela
Group

Harborside Motel & Marina

Hotel with Pools in Key West
Avg. price/night: US$276.81
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 1,300 reviews
nice swimming pool! very friendly staff great picknick tables and other outdoor furniture
Guest review by
Jan
Family with young children

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