Title: Book the Best HISTORIC Hotels in Florida Keys in 2026 | Expedia.ca

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![Higgs Beach which includes a beach and tropical scenes as well as a large group of people](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Florida Keys Historic Hotels

Tonight

[Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Florida Keys historic hotels

![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Street view](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/6177b123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/e65beb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/4a65a2a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pegasus International Hotel

[](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information)

Old Town Key West

8.0/10

Very good

(1,024 reviews)

"Great location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sylvia

CA $392

CA $511 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Room | Courtyard view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/0849ca06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NYAH Key West - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information)

Key West Historic District

8.0/10

Very good

(1,000 reviews)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Venkata Durga Phanindra Reddy

CA $308

CA $410 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/41c85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cottages, dockage, pool, just minutes to Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(121 reviews)

"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ANJANA

CA $278

CA $528 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/4529aa2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1739e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/9ec11af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/72150a37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CORTEZ \~ Adults Only, King Room w/Pool View at Azul Mansion!

[](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.Hotel-Information)

Old Town Key West

9.6/10

Exceptional

(146 reviews)

"Great property. Lots of thoughtful amenities. Management friendly and responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Diane V.

CA $282

CA $550 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/4f32f1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/9d67655b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/4c1d11cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/4c1c78dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Saint Hotel Key West, Autograph Collection, Adult Only

[](https://www.expedia.ca/Key-West-Hotels-The-Saint-Hotel-Key-West.h9650708.Hotel-Information)

Key West Historic District

9.0/10

Wonderful

(347 reviews)

"Great spot!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth

CA $471

CA $530 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Key-West-Hotels-The-Saint-Hotel-Key-West.h9650708.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110840000/110837000/110836928/b1ee0456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110840000/110837000/110836928/52d24796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110840000/110837000/110836928/8eee0984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110840000/110837000/110836928/04380625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TRUMAN ROOM @ Inn on Fleming\~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool

[](https://www.expedia.ca/Key-West-Hotels-TRUMAN-ROOM-Inn-On-FlemingADULTS-ONLY-2nd-Floor-Queen-Shared-Heated-Pool.h110836928.Hotel-Information)

Old Town Key West

9.8/10

Exceptional

(28 reviews)

"Amazing stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Harnoor S.

CA $347

CA $632 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Key-West-Hotels-TRUMAN-ROOM-Inn-On-FlemingADULTS-ONLY-2nd-Floor-Queen-Shared-Heated-Pool.h110836928.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/237d62a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/bd64b13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/8267d923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/55f445db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach! 

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information)

Old Town Key West

9.0/10

Wonderful

(182 reviews)

"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ALISHA

CA $356

CA $663 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/3120319b_edited_07ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/1908c7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/f87deff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed | Bathroom sink](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/634733ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L'Habitation Guest House

[](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.Hotel-Information)

Key West Historic District

9.4/10

Exceptional

(931 reviews)

"Great location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

CA $443

CA $498 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/03c452e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/dcaa469a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/7959b4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/dd3c2d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information)

Tavernier

9.8/10

Exceptional

(210 reviews)

"Absolutely wonderful property in every way!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher K.

CA $417

CA $701 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/b91a3fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/5217059a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/0a4b8784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/w1920h1439x0y1-2c95d321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Key-West-Hotels-LA-DOLCE-VITA.h20480361.Hotel-Information)

Old Town Key West

9.6/10

Exceptional

(146 reviews)

"Perfect apartment for the weekend. It was clean, well decorated and the art work is Key West spectacular. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janet A

CA $372

CA $780 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Key-West-Hotels-LA-DOLCE-VITA.h20480361.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-30&endDate=2026-01-31&regionId=6023765&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Florida Keys Hotel Reviews

![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg)

### Bayside Inn Key Largo

10/10 Excellent

"Spotless rooms, staff is so friendly and helpful! Amazing place to stay."

[](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

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