Find Hotels with a Pool in Key West Historic District, FL from CA $205

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Check prices for these dates

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Nov 11 - Nov 12
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Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Key West Historic District hotels with a pool

A white outdoor seating area with a pool view, featuring white chairs and a small table with a vase of flowers.

1. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
5.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,220 reviews)
The price is CA $367
CA $469 total
includes taxes & fees
Nov 29 - Nov 30
Opal Key Resort & Marina, Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.

2. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,039 reviews)
  • cleanliness
    Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.
The price is CA $216
CA $339 total
includes taxes & fees
Dec 2 - Dec 3
Silver Palms Inn & Historic Homes
A pool area with lounge chairs and a cabana.

3. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Float in the outdoor pool with Key West sunset views, poolside loungers, and bar service for luxury.
The price is CA $361
CA $521 total
includes taxes & fees
Nov 29 - Nov 30
Ocean Key Resort - A Noble House Resort
A poolside area with wicker furniture, a covered seating area, and a white building with a balcony.

4. Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Take a dip in Key West's serene outdoor pool oasis, where relaxation meets historic charm just steps from Duval Street.
The price is CA $282
CA $389 total
includes taxes & fees
Dec 1 - Dec 2
Lighthouse Hotel - Key West Historic Inns
A pool area with a pink canopy, lounge chairs, and a seating area with cushions.

5. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Key West Historic District
8.8 out of 10, Excellent, (516 reviews)
  • cleanliness
    Relaxing poolside retreat in vibrant Key West with easy access to Duval Street and walking distance to all attractions.
The price is CA $294
CA $378 total
includes taxes & fees
Dec 1 - Dec 2
La Concha Key West, Autograph Collection
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

6. Duval House

Duval House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,139 reviews)
  • cleanliness
    Soothing heated pool in the heart of Key West creates an inviting oasis amid tropical gardens at this bed and breakfast.
The price is CA $240
CA $300 total
includes taxes & fees
Nov 18 - Nov 19
Duval House
A hotel with a swimming pool, balconies, and a view of the sea.

7. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,004 reviews)
The price is CA $342
CA $489 total
includes taxes & fees
Nov 29 - Nov 30
Hyatt Centric Key West Resort and Spa
A pool area with lounge chairs and a building with blue lighting.

8. The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Key West Historic District
9.0 out of 10, Wonderful, (378 reviews)
The price is CA $301
CA $338 total
includes taxes & fees
Dec 8 - Dec 9
The Saint Hotel Key West, Autograph Collection, Adult Only
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

9. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,049 reviews)
  • cleanliness
    Splash into bliss at this harbour resort offering three pools, a poolside bar, and daily live entertainment.
The price is CA $330
CA $464 total
includes taxes & fees
Nov 17 - Nov 18
The Marker Key West Harbor Resort
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

10. Tropical Inn

Tropical Inn
3.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (457 reviews)
The price is CA $206
CA $267 total
includes taxes & fees
Nov 15 - Nov 16
Tropical Inn
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.
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Compare popular hotels in Key West Historic District

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
Silver Palms Inn & Historic Homes
3.5 star property
9.4
Exceptional
1,039 reviews
View
A multi-story hotel with a pink facade, multiple balconies, and a prominent 'LA CONCHA' sign.
La Concha Key West, Autograph Collection
4.0 star property
8.8
Excellent
516 reviews
View
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
Duval House
3.0 star property
9.6
Exceptional
1,139 reviews
View
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
Lighthouse Hotel - Key West Historic Inns
3.5 star property
9.0
Wonderful
1,000 reviews
View
A pool area with lounge chairs and a cabana.
Ocean Key Resort - A Noble House Resort
4.0 star property
9.2
Wonderful
1,000 reviews
View

Top Key West Historic District Hotel Reviews

A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Old Town Key West

10/10 Excellent

Had a great time! Very nice place to stay!
Canada
Gordon Christopher
Reviewed August 24, 2026
Orchid Key Inn - Adults Only

Frequently Asked Questions

How many hotels with pools will I find in Key West Historic District?

Expedia's 146 hotels in Key West Historic District give you a great choice for your poolside getaway.

What's it like visiting Key West Historic District?

If lounging next to a pool is your idea of the perfect getaway, you may want to consider Key West Historic District, which offers 146 places to stay with pools. While you're visiting, you can explore attractions like Duval Street and Florida Keys Beaches, and then relax poolside at one of the accommodations in Key West Historic District that guests like for their pools.

What are some accommodations with pools in Key West Historic District?

Winslow's Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Features complimentary wireless internet access, 3 outdoor pools, and LED televisions. The Reach Key West, Curio Collection by Hilton: Resort, 3-minute walk from Duval Street. Offers a private beach, an outdoor pool, and a full-service spa. Opal Key Resort & Marina, Key West: Hotel steps from Mallory Square. Provides 3 bars, an outdoor pool, and spa services. La Concha Key West, Autograph Collection: Hotel, 1-minute walk from Duval Street. Features 3 restaurants, an outdoor pool, and 2 bars. Hyatt Centric Key West Resort and Spa: Resort, 1-minute walk from Florida Keys Beaches. Offers a full-service spa, a pool, and a snack bar/deli.

What is there to see and do in Key West Historic District?

Explore places like Duval Street and Florida Keys Beaches while you're in Key West Historic District. The picturesque setting of Key West Butterfly and Nature Conservatory and South Beach showcase the area’s natural beauty. Key West Historic District appeals to visitors with its bar scene and great live music scene.

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