Find Historic Hotels in Florida Keys

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Check availability on Florida Keys Historic Hotels

Tonight
7 Feb - 8 Feb
Tomorrow
8 Feb - 9 Feb
Next weekend
13 Feb - 15 Feb
In two weeks
20 Feb - 22 Feb

Our top choices for Florida Keys historic hotels

Outdoor dining

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is AED 661
AED 1,190 total
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
Sundeck

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1,008 reviews)
"Very clean, great amenities! "
United States
Heather
Pegasus International Hotel
TV

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Old Town Key West
9.6 out of 10, Exceptional, (158 reviews)
"Had a wonderful visit and everything was amazing I would highly recommend this place "
United States
Joel
The price is AED 789
AED 1,507 total
includes taxes & fees
9 Feb - 10 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
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, (118 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 890
AED 1,689 total
includes taxes & fees
10 Feb - 11 Feb
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
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, (213 reviews)
"Absolutely wonderful property in every way!"
United States
Christopher K.
The price is AED 1,466
AED 2,293 total
includes taxes & fees
11 Mar - 12 Mar
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Front of property

Grand Maloney Hotel

Grand Maloney Hotel
2.0 star property
Key West Historic District
7.8 out of 10, Good, (13 reviews)
"Excellent location in old town. Quiet room away from street. "
United States
James
The price is AED 1,608
AED 2,438 total
includes taxes & fees
2 Mar - 3 Mar
Grand Maloney Hotel
Beach towels

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

'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Old Town Key West
9.6 out of 10, Exceptional, (38 reviews)
"Convenient, clean….nice neighborhood."
United States
Anna H.
The price is AED 1,084
AED 2,188 total
includes taxes & fees
9 Mar - 10 Mar
'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Outdoor dining

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very Good, (121 reviews)
"Great experience "
United States
Peyton S.
The price is AED 1,286
AED 2,559 total
includes taxes & fees
22 Feb - 23 Feb
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Property grounds

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is AED 1,506
AED 2,840 total
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is AED 1,377
AED 2,674 total
includes taxes & fees
21 Feb - 22 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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

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