Find Hotels with a Pool in Key West Historic District, FL

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Pick from 60 Key West Historic District Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Silver Palms Inn
Outdoor pool
Silver Palms Inn
3.5 star property
9.2 out of 10, Wonderful, (1005)
"Great place to stay"
The price is NT$5,392
NT$7,861 total
includes taxes & fees
Nov 6 - Nov 7
Silver Palms Inn
The Southernmost Inn - Adults Only
Building design
The Southernmost Inn - Adults Only
3.0 star property
8.0 out of 10, Very Good, (1001)
"Checking was a breeze and the hot tub was epic! We are a couple of happy campers!!!"
The price is NT$5,392
NT$7,501 total
includes taxes & fees
Nov 6 - Nov 7
The Southernmost Inn - Adults Only
Pier House Resort & Spa
Outdoor pool, pool umbrellas, sun loungers
Pier House Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (1004)
"Best location to stay and enjoy the Island, from dining to drinking to quiet sunset at Mallory Square."
The price is NT$14,337
NT$18,140 total
includes taxes & fees
Nov 18 - Nov 19
Pier House Resort & Spa
The Cabana Inn Key West - Adults Only
Exterior
The Cabana Inn Key West - Adults Only
3.0 star property
8.8 out of 10, Excellent, (1000)
"Great spot ,great staff."
The price is NT$5,075
NT$7,145 total
includes taxes & fees
Nov 6 - Nov 7
The Cabana Inn Key West - Adults Only
Winslow's Bungalows - Key West Historic Inns
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns
4.0 star property
9.0 out of 10, Wonderful, (930)
"Loved the location…quiet but soooo close to everything!"
The price is NT$9,907
NT$12,473 total
includes taxes & fees
Nov 18 - Nov 19
Winslow's Bungalows - Key West Historic Inns
The Marker Key West Harbor Resort
3 outdoor pools, pool umbrellas, sun loungers
The Marker Key West Harbor Resort
4.0 star property
8.8 out of 10, Excellent, (1000)
"We make every attempt to stay at the Marker when we travel to Key West. You won't be disappointed staying here. Im"
The price is NT$7,716
NT$10,619 total
includes taxes & fees
Dec 1 - Dec 2
The Marker Key West Harbor Resort
Ocean Key Resort - A Noble House Resort
Outdoor pool, sun loungers
Ocean Key Resort - A Noble House Resort
4.0 star property
9.2 out of 10, Wonderful, (1004)
"Staff were all GREAT! The room was very clean and large. Pool wasn’t big but was never so busy we couldn’t get chairs. Definitely check out the Hot Tin Roof bar and restaurant. Best Peaches and Cream Old Fashioned! Best drink I had in Key West! Overall, would stay again and would recommend! "
The price is NT$10,826
NT$14,333 total
includes taxes & fees
Nov 20 - Nov 21
Ocean Key Resort - A Noble House Resort
La Concha Key West
Penthouse, 1 King Bed, View, Corner | Premium bedding, pillowtop beds, minibar, in-room safe
La Concha Key West
4.0 star property
8.0 out of 10, Very Good, (1126)
"Richard immediately greeted us with a smile when we arrived. He was most helpful with getting us bikes and drove us on a golf cart to the sister hotel, The Marker, to use their pool since La Concha pool will not reopen until next week. The decor was beautiful , with a Cuban vibe. Great location."
The price is NT$8,109
NT$10,079 total
includes taxes & fees
Dec 1 - Dec 2
La Concha Key West
NYAH Key West - Adults Only
Outdoor spa tub
NYAH Key West - Adults Only
3.0 star property
7.6 out of 10, Good, (999)
"Place is excellent and safe"
The price is NT$3,478
NT$5,348 total
includes taxes & fees
Nov 11 - Nov 12
NYAH Key West - Adults Only
H2O Suites - Adults Only
Deluxe Suite, 1 King Bed, Private Pool | View from room
H2O Suites - Adults Only
3.5 star property
9.8 out of 10, Exceptional, (519)
"awesome hotel "
The price is NT$13,049
NT$16,116 total
includes taxes & fees
Nov 11 - Nov 12
H2O Suites - Adults Only
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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Frequently asked questions

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 222 places to stay with pools. While you’re visiting, you can explore attractions like Duval Street and Mallory Square, 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?
Southernmost Beach Resort: Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. Winslow’s Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Offers daily, 3 outdoor pools, and complimentary wireless internet access. Opal Key Resort & Marina, Key West: Hotel steps from Mallory Square. Provides 3 bars, an outdoor pool, and spa services. The Reach Key West, Curio Collection by Hilton: Hotel steps from South Beach. Features a private beach, an outdoor pool, and a full-service spa. Lighthouse Hotel - Key West Historic Inns: Hotel steps from Ernest Hemingway Home and Museum. Offers daily, an outdoor pool, and complimentary wireless internet access.
How many hotels with pools will I find in Key West Historic District?
Expedia’s 222 hotels in Key West Historic District give you a great choice for your poolside getaway.
What is there to see and do in Key West Historic District?
Explore places like Duval Street and Mallory Square while you’re in Key West Historic District. The picturesque setting of Audubon House and Tropical Gardens and Key West Butterfly and Nature Conservatory showcase the area’s natural beauty. Key West Historic District appeals to visitors with its bar scene and great live music scene.