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

Historic Hotels & Resorts in Florida Keys from AU$220

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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 reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A hotel lobby with a bar area, seating, and a fireplace.
A bar area with a Pegasus International Hotel sign, round tables, and metal chairs.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
AU$241
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.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
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
AU$220
includes taxes & fees
28 Sept - 29 Sept
Amsterdam's Curry Mansion Inn
A covered outdoor area with wicker furniture and a pool.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A beach with palm trees and a clear sky.
A wooden staircase with a view of greenery outside.

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
AU$388
includes taxes & fees
29 Sept - 30 Sept
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
A narrow pathway flanked by white picket fences and a tree with pink flowers.
A covered porch with white railings and wicker furniture.
A compact kitchen with a microwave, refrigerator, and a sink.
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.
AU$553
includes taxes & fees
6 Oct - 7 Oct
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
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.
AU$499
includes taxes & fees
29 Sept - 30 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.
A coffee shop interior with a wooden counter, a coffee machine, and a display case with pastries.
An outdoor bar area with wooden chairs, a bar counter, hanging lights, and a water feature.
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.
AU$638
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 living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
A pathway through a lush garden with various plants and trees.
A bar with a signboard listing various destinations.

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
AU$730
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 kitchen counter with a woven basket containing fruits, a potted plant, and a small wooden box.

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 covered porch with white chairs and a table, overlooking a tropical landscape with palm trees and a beach.
A living room with a red sofa, a white armchair, a round coffee table, and a potted plant.
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
AU$676
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 living room with a sofa, coffee table, TV, and cabinets.
An aerial view of a resort with a central swimming pool, surrounded by palm trees and a large building with multiple windows.
A beach setting with Adirondack chairs arranged around a fire pit, a thatched-roof structure, and string lights.

10. Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
United States
Georgi T.
Key largo Kawama Villa N2
View all properties

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

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