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

Find Historic Hotels in Florida Keys from CA $249

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Check availability on Florida Keys Historic Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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
CA $158
CA $249 total
includes taxes & fees
Oct 11 - Oct 12
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
Tiffany N
CA $265
CA $442 total
includes taxes & fees
Oct 14 - Oct 15
Amsterdam's Curry Mansion Inn
A living room with two sofas, a coffee table, and a window with blinds.
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. HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
Old Town Key West
United States
Vicki L.
CA $155
CA $393 total
includes taxes & fees
Oct 12 - Oct 13
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A compact kitchen with a microwave, oven, and sink. There is a small dining table with a bowl and a chair. The kitchen has light blue tiles and wooden cabinets.
A well-lit bedroom with a large bed, a desk, a chair, and a sofa. There are multiple pillows, a lamp, and a plant on the bedside table.

4. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
CA $265
CA $553 total
includes taxes & fees
Oct 26 - Oct 27
Studio Blu - Historic Key West Studio + Bikes
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A bar with a signboard listing various destinations.
A pathway through a lush garden with various plants and trees.
A two-story house with a front porch, a staircase, and a garage.

5. 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
CA $301
CA $742 total
includes taxes & fees
Oct 12 - Oct 13
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.

6. Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
United States
Diana
CA $380
CA $824 total
includes taxes & fees
Oct 18 - Oct 19
Key Largo Kawama villa K1, 3/3
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 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.
A coffee shop interior with a wooden counter, a coffee machine, and a display case with pastries.

7. 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.
CA $352
CA $627 total
includes taxes & fees
Oct 14 - Oct 15
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
A person swimming with a large, spiky, orange object.
A covered wooden deck with white railings, leading to a building with green-framed windows.
A beach with clear water and gentle waves.
A yellow building with a balcony, parked cars, and palm trees.

8. 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
United States
Kayleigh V.
CA $462
CA $871 total
includes taxes & fees
Oct 11 - Oct 12
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.
An open door to a room with a bed, a heart-shaped pillow, and a painting on the wall.
A room with a bed, a dining table, and a kitchen area.

9. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
CA $468
CA $593 total
includes taxes & fees
Oct 15 - Oct 16
Poolside Studio Villa Steps from Duval!
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.
A bedroom with a wooden bed, two nightstands with lamps, a ceiling fan, and decorative plates on the wall.
A cozy dining area with a wooden table, wicker chairs, and a bowl of fruit. There is a ceiling fan and a colorful wall decoration.

10. Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
United States
Matt S.
CA $897
CA $1,137 total
includes taxes & fees
Oct 29 - Oct 30
Two Bedroom Two Bath Poolside Villa Steps from Duval!
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Top Florida Keys Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Our room was very clean. Resort staff was super nice and accommodating. Amenities were nice. Pools were clean. Resort was very peaceful."
Grayson 5-night trip
Posted 12 hours ago
Islander Resort

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