A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Florida Keys Hotel Guide - Historic Hotels in Florida Keys, United States of America

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Check availability on Florida Keys Historic Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Florida Keys historic hotels

A balcony with a view of a street, a bench, and a potted plant.
A multi-story building with a ground-level commercial space featuring a brightly lit storefront.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A hotel lobby with a bar area, seating, and a fireplace.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
€153
includes taxes & fees
1 Oct - 2 Oct
Pegasus International Hotel
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
€139
includes taxes & fees
28 Sept - 29 Sept
Amsterdam's Curry Mansion Inn
A covered outdoor area with wicker furniture and a pool.
A wooden staircase with a view of greenery outside.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

3. COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!

COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
Old Town Key West
United States
Patrick
€248
includes taxes & fees
29 Sept - 30 Sept
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.
A compact kitchen with a microwave, refrigerator, and a sink.
A narrow pathway flanked by white picket fences and a tree with pink flowers.
A living room with a red leather sofa, a white armchair, and a small round table.

4. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
United States
Michael R.
€341
includes taxes & fees
6 Oct - 7 Oct
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A neatly made bed with a patterned bedspread, a decorative pillow, and two bedside lamps on either side.
A bedroom with a wooden bed, a desk, a chair, a wardrobe, and a nightstand with a lamp.
A bathroom with a bathtub, toilet, sink, and shower curtain.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
€319
includes taxes & fees
28 Sept - 29 Sept
Studio Blu - Historic Key West Studio + Bikes
A compact kitchen with a dishwasher, a microwave, and a sink. There is a window with a view of the outdoors, and a ceiling fan.
An outdoor bar area with wooden chairs, a bar counter, hanging lights, and a water feature.
A yacht docked at a marina with a wooden deck, a pool, and string lights.
A balcony with a view of a marina, a wooden chair, a potted plant, and a welcome mat.

6. 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
United States
Michelle P.
€405
includes taxes & fees
27 Sept - 28 Sept
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A pathway through a lush garden with various plants and trees.
A bar with a signboard listing various destinations.
A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.

7. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
United States
Linda
€460
includes taxes & fees
27 Sept - 28 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A modern kitchen with a large island, a dining area with a sofa, and a view of the outdoors.
A beach setting with a thatched umbrella, a table with chairs, and a view of the sea.
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.
A modern kitchen with white cabinets, a stainless steel dishwasher, a central island with a woven basket, and a coffee maker.

8. Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
United States
Diana
Key Largo Kawama villa K1, 3/3
A beach with clear turquoise water, a sandy shore, and a few people swimming.
A living room with a red sofa, a white armchair, a round coffee table, and a potted plant.
A covered porch with white chairs and a table, overlooking a tropical landscape with palm trees and a beach.
A narrow pathway flanked by white picket fences and a tree with pink flowers.

9. STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH

STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
Old Town Key West
United States
Joseph
€420
includes taxes & fees
6 Oct - 7 Oct
STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
A beach setting with a thatched umbrella, a small round table, and two chairs.
A beach setting with Adirondack chairs arranged around a fire pit, a thatched-roof structure, and string lights.
An aerial view of a resort with a central swimming pool, surrounded by palm trees and a large building with multiple windows.
A modern kitchen with white cabinetry, stainless steel appliances, a central island with seating, and a window providing a view.

10. Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
United States
Georgi T.
Key largo Kawama Villa N2
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Top Florida Keys Hotel Reviews

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great location !!"
Jenny 2-night trip
Posted 1 hour ago
Bayside Inn Key Largo