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Our top choices for Florida Keys historic hotels

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1,003 reviews)
"Our absolute favorite place to stay when in Key West 10/10 hands down Great location, the friendliest staff, & a nice breakfast selection each morning Look no further "
United States
Amanda Tyie
The price is ¥24,900
¥35,997 total
includes taxes & fees
May 7 - May 8
Pegasus International Hotel

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.2 out of 10, Very Good, (1,004 reviews)
"The location was great. The bed was comfortable."
United States
Frances
The price is ¥37,550
¥42,244 total
includes taxes & fees
May 11 - May 12
Amsterdam's Curry Mansion Inn

FUENTE ~ Adults Only, 2nd Level Pool View King Room at Azul Mansion!

FUENTE ~ Adults Only, 2nd Level Pool View King Room at Azul Mansion!
Old Town Key West
9.6 out of 10, Exceptional, (143 reviews)
"Host was great. Rooms well appointed and clean. Great location"
United States
Peter B.
The price is ¥18,437
¥45,131 total
includes taxes & fees
May 10 - May 11
FUENTE ~ Adults Only, 2nd Level Pool View King Room at Azul Mansion!

The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Key West Historic District
9.0 out of 10, Wonderful, (362 reviews)
"We loved the Saint Hotel and the staff was amazing! Will definitely be back! Perfect location. "
United States
Tunya
The price is ¥41,349
¥46,517 total
includes taxes & fees
May 13 - May 14
The Saint Hotel Key West, Autograph Collection, Adult Only

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (246 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is ¥23,989
¥55,478 total
includes taxes & fees
May 18 - May 19
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Old Town Key West
9.8 out of 10, Exceptional, (43 reviews)
"Great location, one block from Duval Street but still quiet, clean and comfortable. "
United States
Jackie H.
The price is ¥26,413
¥67,586 total
includes taxes & fees
May 30 - May 31
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (120 reviews)
"Brilliant location… very generous to leave bikes and chairs which was used every day. Well decorated and equipped room and comfy bed . Shower is hot and has great water pressure . Check in and out is easy . Thank you "
United Kingdom
Simon
The price is ¥28,776
¥58,871 total
includes taxes & fees
May 10 - May 11
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (217 reviews)
"Our stay was amazing, I highly recommend Heidi and this location!"
United States
Becky S.
The price is ¥43,373
¥74,583 total
includes taxes & fees
May 17 - May 18
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.6 out of 10, Exceptional, (134 reviews)
"The condo was perfectly appointed with everything we would want or need, including some snorkel masks, beach towels, bikes. Really a wonderful stay. Thanks."
United States
Wendy R.
The price is ¥52,001
¥102,953 total
includes taxes & fees
May 19 - May 20
Key largo Kawama Villa N2

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Old Town Key West
9.2 out of 10, Wonderful, (299 reviews)
"The host was super! The place was clean and in a great location. Very quiet, too. Loved our stay. Patt"
United States
Patricia P.
The price is ¥51,259
¥96,939 total
includes taxes & fees
Jun 1 - Jun 2
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
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 Florida Keys Hotel Reviews