Find Historic Hotels in Florida Keys

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Check availability on Florida Keys Historic Hotels

Our top choices for Florida Keys historic hotels

Sundeck

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1,006 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 AED 580
AED 838 total
includes taxes & fees
10 May - 11 May
Pegasus International Hotel
Exterior

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 AED 966
AED 1,087 total
includes taxes & fees
31 May - 1 Jun
The Saint Hotel Key West, Autograph Collection, Adult Only
Terrace/patio

FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!

FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!
Old Town Key West
9.4 out of 10, Exceptional, (145 reviews)
"All was great. Very convenient location and Key West vibe. "
United States
laurie y.
The price is AED 391
AED 1,004 total
includes taxes & fees
12 May - 13 May
FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!
Beach nearby, white sand, beach cabanas, sun loungers

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, (1,006 reviews)
"This is our favorite place to stay! Great location and perfect accommodations for a trip to Key West!"
United States
Patti
The price is AED 829
AED 933 total
includes taxes & fees
20 May - 21 May
Amsterdam's Curry Mansion Inn
Beach

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, (248 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Exterior detail

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 AED 710
AED 1,460 total
includes taxes & fees
8 Jun - 9 Jun
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Beach towels

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 AED 617
AED 1,579 total
includes taxes & fees
30 May - 31 May
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Fridge, microwave, oven, stovetop

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 AED 1,010
AED 1,737 total
includes taxes & fees
17 May - 18 May
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Smart TV

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 AED 1,145
AED 2,328 total
includes taxes & fees
11 May - 12 May
Key largo Kawama Villa N2
Sun loungers, beach towels

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, (300 reviews)
"Great place. Walking distance to everything! Would highly recommend!"
United States
Leslie S.
The price is AED 1,194
AED 2,258 total
includes taxes & fees
6 Jun - 7 Jun
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.
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Top Florida Keys Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"The resort is truly a tropical paradise."
TAXAID 1-night trip
Posted 19 hours ago
Islander Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

8/10 Good
"Location and amenities are Great. We really enjoyed sitting on the beach for the sunset."
Kimberly 1-night trip
Posted 2 days ago
Bayside Inn Key Largo

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