Title: Book the Best Hotels with POOL in Downtown Key West in 2026 | Expedia.ca

[Downtown Key West Travel Guide](https://expedia.ca/Key-West-Downtown-Key-West.dx553248635976470405)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Downtown Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Key-West.d553248635976470405.Car-Rental-Guide)[Downtown Key West Vacations](https://expedia.ca/Downtown-Key-West.d553248635976470405.Destination-Travel-Guides)

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# Find Hotels with a Pool in Downtown Key West, FL from CA $214

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## Check availability on Downtown Key West Hotels with a Pool

Tonight

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Downtown Key West hotels with a pool

![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/1fc21e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Duval Duplex 2 bedrooms 25 ft Balcony (Adults Only) | Living area](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/83acfbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9ce49b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Duval House

[](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

Old Town Key West

9.4/10

Exceptional

(1010)

"I loved this place the location was absolutely perfect "

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

Frank

CA $164

CA $214 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

![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)

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

![Tropical King](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/84d1a4db.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)

### 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)

![Sports facility](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/34315005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![11 Gecko's Garden - Adults Only](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/5a952061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poinciana Patio, Pool View, Patio - Adult Only | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/a07e6903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/4d274a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical Inn

[](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information)

Old Town Key West

9.6/10

Exceptional

(363)

"The place was excellent and the service amazing "

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

Janae

CA $236

CA $299 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/580edbc7.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)

![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)

![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)

### Pegasus International Hotel

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

Old Town Key West

8.2/10

Very good

(1003)

"Wonderful place to stay right in the heart of Key West. The pool and deck area are nice and cozy for a relaxing time. "

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

Daniel

CA $199

CA $294 total

includes taxes & fees

Dec 17 - Dec 18

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/cb58ce3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/37c4e4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/f9d7e75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/750d9b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Almond Tree Inn Hotel - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information)

Old Town Key West

10/10

Exceptional

(1001)

"Very nice & peaceful with a wonderful staff. Our second time staying here"

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

Sandra

CA $313

CA $352 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/872463e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Bedrooms (Royal Poinciana) | Living area](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/bab228c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/d1b7d1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/e882a768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise Inn Key West - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information)

Old Town Key West

9.2/10

Wonderful

(1004)

"Cozy place right near everything "

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

Joseph

[](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information)

![Cabana King, Accessible | Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/7de720ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/4d2c753c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabana Cottage](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/75209084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/8cc28f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cabana Inn Key West - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information)

Old Town Key West

8.8/10

Excellent

(1005)

"Nice place "

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

Suzanne

CA $160

CA $242 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information)

![Poolside bar](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/c8bd1ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Havana Suite w/kitchenette | Garden view](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/6c9ccbbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/0655c71e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room,w/balcony. 1 King Bed](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/f9abeb6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Duval Inn

[](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information)

Old Town Key West

8.6/10

Excellent

(717)

"Property was clean and perfect location."

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

Tracy

CA $639

CA $789 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/bcca482f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/4f0962a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Paris | Room amenity](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/7455b830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Malaga | View from room](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/5c7fe792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Andrews Inn & Garden Cottages

[](https://www.expedia.ca/Key-West-Hotels-Andrews-Inn-Garden-Cottages.h19690128.Hotel-Information)

Old Town Key West

9.0/10

Wonderful

(265)

"Easy to access and a peaceful place. I’ll definitely come back."

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

Jessica

CA $356

CA $432 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Andrews-Inn-Garden-Cottages.h19690128.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/7e102845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/ec642303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/b83c4cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/a17d99e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coco Plum Inn

[](https://www.expedia.ca/Key-West-Hotels-Coco-Plum-Inn.h2231933.Hotel-Information)

Old Town Key West

9.6/10

Exceptional

(464)

"It was a lovely day at the Cocoa plum inn. The location was perfect and the grounds were cleanz, staffl was great!"

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

Diane

CA $222

CA $250 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Coco-Plum-Inn.h2231933.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=553248635976470405&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Downtown Key West Hotel Reviews

![The Cabana Inn Key West - Adults Only](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65_y.jpg)

### The Cabana Inn Key West - Adults Only

10/10 Excellent

"Breakfast was fresh daily, we did not have a vehicle, but all places were easily accessible."

[](https://expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information)

![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)

![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg)

### Duval House

10/10 Excellent

"The garden area was fabulous "

[](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

![Wicker Guesthouse](https://images.trvl-media.com/lodging/11000000/10980000/10974500/10974431/f74278e9_y.jpg)

### Wicker Guesthouse

10/10 Excellent

"So quiet, quaint and clean!"

[](https://expedia.ca/Key-West-Hotels-Wicker-Guesthouse.h10974431.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)

![Heron House - Adult Only](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1_y.jpg)

### Heron House - Adult Only

10/10 Excellent

"Yes"

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

![Paradise Inn Key West - Adults Only](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/069168f1_y.jpg)

### Paradise Inn Key West - Adults Only

10/10 Excellent

"Staff was amazing! Pool was warm and everything was beautiful "

[](https://expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information)

## Frequently asked questions

### What's it like visiting Downtown Key West?

### What are some hotels with pools in Downtown Key West?

### How many pool hotels are there in Downtown Key West?

### What is there to see and do in Downtown Key West?

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