Title: Book the Best HISTORIC Hotels in Dredgers Key in 2026 | Expedia.ca

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![Sailboat Anchored off coast of Dredger Key Sigsbee - Key West Florida](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Historic Hotels in Dredgers Key, FL from CA $228

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## Check availability on Dredgers Key Historic Hotels

Tonight

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Dredgers Key historic hotels

![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)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.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)

![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.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

(120)

"Jennifer was very nice and accommodating."

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

Randy G.

CA $220

CA $454 total

includes taxes & fees

Dec 17 - Dec 18

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

![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/25b961c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/caa3fc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/e1365b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/1577bf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint cottage, pool, dockage just minutes to Key West!

[](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(146)

"great location, we are return visitors & will be back!"

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

Shannon W.

CA $379

CA $655 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information)

![Queen with Pool View](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/2d84982c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe King Suite H | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/cc10991a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/4d67c395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/49f6e3c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Simonton Court Historic Inn & Cottages

[](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.Hotel-Information)

Key West Historic District

9.8/10

Exceptional

(879)

"The staff was really nice"

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

doug

CA $205

CA $231 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.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)

![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)

![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 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

(1004)

"Great little hotel in the heart of Old Town."

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

Robert

CA $147

CA $228 total

includes taxes & fees

Dec 17 - Dec 18

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

![Exterior](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a156943e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/af6258cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a15e99ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/1e9c6159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Marker Key West Harbor Resort

[](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information)

Key West Historic District

9.2/10

Wonderful

(1008)

"Fantastic staff, great breakfast"

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

Kelly

CA $296

CA $420 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/f02c0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tropical King](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/7d668ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/002755fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/617f7c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heron House Court - Adult Only

[](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information)

Key West Historic District

9.0/10

Wonderful

(1009)

"Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. "

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

Chandler

CA $383

CA $483 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach towels, scuba diving, snorkeling](https://images.trvl-media.com/lodging/1000000/10000/1000/901/5e1da484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed, Ocean View](https://images.trvl-media.com/lodging/1000000/10000/1000/901/085b3544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/1000000/10000/1000/901/391bc96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Key West Resort and Spa

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information)

Key West Historic District

9.0/10

Wonderful

(1011)

"Staff was courteous and the location is perfect for a weekend in Key West."

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

TIMOTHY

CA $329

CA $460 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/841e73b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/0acd853b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Opal Key Resort & Marina, Key West

[](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information)

Old Town Key West

9.2/10

Wonderful

(1023)

"Our stay was great!"

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

Richard

CA $384

CA $486 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/3e2c6b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/e213aee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually decorated, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/6eb12223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heron House - Adult Only

[](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information)

Old Town Key West

9.0/10

Wonderful

(1137)

"Loved the setup of the hotel and great location! "

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

Rachel

CA $451

CA $561 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/d5932f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cozy King ](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/998684c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/b69fa79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room | Property entrance](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/d2f1234b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Garden House

[](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information)

Key West Historic District

9.2/10

Wonderful

(668)

"It a small convenient location and walkable to great areas. "

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

Manuel

CA $178

CA $229 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.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=2025-12-30&endDate=2025-12-31&regionId=180165&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Dredgers Key Hotel Reviews

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg)

### Blue Flamingo Resort Key West

10/10 Excellent

"."

[](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information)

![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg)

### DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"shuttle"

[](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information)

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg)

### Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Beach and pool - bar, music and great staff"

[](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information)

![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg)

### Pier House Resort & Spa

10/10 Excellent

"Clean room, great amenities, very nice staff and close by foot to restaurants and stores."

[](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information)

![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg)

### Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel."

[](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information)

![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg)

### La Concha Key West, Autograph Collection

10/10 Excellent

"My husband and I enjoyed our stay at the hotel tremendously - everything was excellent! Location, cleanliness, pool, food, bedding, friendly staff, hotel decor, pleasant ambiance. Highly recommend this hotel to the guests who want to experience upscale services and hospitality of old Florida"

[](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information)

![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg)

### Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"Quaint hotel with beautiful grounds. Close to everything yet far away enough away from Duvall. Clean and comfortable rooms"

[](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information)

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg)

### Beachside Resort & Residences

10/10 Excellent

"The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area "

[](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information)

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg)

### Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Beautiful place"

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information)

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