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Hotels with Entertainment in Key West, Florida

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Check availability on Key West Hotels with Entertainment

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Key West hotels with entertainment

Outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas, sun loungers

1. Tranquility Guest House

Tranquility Guest House
2.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (9 reviews)
"It was a great property, very clean room and excellent price. Staff was great."
United States
Hector
The price is P5,095
P11,176 total
includes taxes & fees
Aug 31 - Sep 1
Tranquility Guest House
Minibar, in-room safe, iron/ironing board, WiFi (free)

2. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (1,001 reviews)
"Always a great stay!!"
United States
Robin
The price is P10,966
P12,337 total
includes taxes & fees
Aug 2 - Aug 3
Simonton Court Historic Inn & Cottages
2 outdoor pools, open 7:00 AM to 10:00 PM, cabanas (surcharge)

3. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.6 out of 10, Excellent, (2,597 reviews)
"Great place to stay."
United States
Robert
The price is P7,394
P11,764 total
includes taxes & fees
Sep 1 - Sep 2
Blue Flamingo Resort Key West
Porch

4. Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,168 reviews)
"Great stay highly recommended"
United States
Lindsay
The price is P7,287
P10,241 total
includes taxes & fees
Aug 2 - Aug 3
Heron House - Adult Only
Restaurant

5. Artist House Key West

Artist House Key West
3.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (451 reviews)
"Great atmosphere and location."
United States
NATHAN
The price is P8,298
P9,335 total
includes taxes & fees
Aug 19 - Aug 20
Artist House Key West
Exterior

6. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (469 reviews)
"Gorgeous property with beautiful grounds!"
United States
Kevin
The price is P7,147
P8,845 total
includes taxes & fees
Aug 3 - Aug 4
Douglas House - Adults Only
Front of property - evening/night

7. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,174 reviews)
"The location is fantastic-hotel and staff were great ."
United States
Marion
The price is P15,867
P20,263 total
includes taxes & fees
Aug 6 - Aug 7
Opal Key Resort & Marina, Key West
Outdoor pool, free cabanas, sun loungers

8. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,003 reviews)
"Loved staying here, super convenient location and having the lobby bar was wonderful at the end of the day!"
United States
Stephanie
The price is P13,487
P19,929 total
includes taxes & fees
Aug 16 - Aug 17
Ocean Key Resort - A Noble House Resort
City view

9. Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place. Just wish they had a dock for fishing."
United States
Marcia
The price is P7,939
P11,701 total
includes taxes & fees
Aug 3 - Aug 4
Paradise Inn Key West - Adults Only
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)

10. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town
8.0 out of 10, Very Good, (1,284 reviews)
"Great place to stay for a weekend"
United States
Oscar
The price is P7,834
P10,537 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Key West / The Keys Collection
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.
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Top Key West Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"The property was very nice but in need a daily maintenance: Lawn cleaned and mowed to keep up resort type appearance that it should. Probably should hose off the stairs and benches of chicken droppings, also to look resort worthy. All said and done, the room was exceptionally nice (ice maker didn't work) and the amenities were good - though some beach chairs were broken however it is noted, some of the tourist around the pool were nasty and there were kids jumping on those chairs. It is a good location, easy to go anywhere and the restaurant was very nice."
Karl 7-night trip
Posted 2 hours ago
Beachside Resort & Residences