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, (1007)
"Great place. Off the beaten path. If you like that, you will love this spot."
The price is NT$5,167
NT$7,641 total
includes taxes & fees
Dec 1 - Dec 2
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, (1014)
"cottsge type layout "
The price is NT$4,199
NT$6,188 total
includes taxes & fees
Nov 24 - Nov 25
The Southernmost Inn - Adults Only
Pier House Resort & Spa
Outdoor pool, pool umbrellas, sun loungers
Pier House Resort & Spa
4.0 star property
9.0 out of 10, Wonderful, (1011)
"The Location was excellent! Everyone here was very knowledgeable, nice, and helpful! This place had everything you need! Restaurants, bars, pool, spa, and a private beach, And it was close and walkable to many restaurants, historical sites, retail shops, music, and more! We look forward to staying here again! "
The price is NT$7,484
NT$10,466 total
includes taxes & fees
Dec 1 - Dec 2
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)
"Perfect location. If you want to be able to walk around Key West this is the place. The coffee machine is fabulous. There is free breakfast and wine and cheese at 5pm.It has a communal atmosphere with rooms around the pool."
The price is NT$5,817
NT$8,006 total
includes taxes & fees
Nov 23 - Nov 24
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, (949)
"Excellent choice for location, amenities and overall ambience with historical vibes. Staff was stellar."
The price is NT$10,054
NT$12,663 total
includes taxes & fees
Dec 1 - Dec 2
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, (1004)
"Location was outstanding and staff was exceptional. "
The price is NT$8,132
NT$11,122 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, (1003)
"Liked everything Great staff"
The price is NT$8,937
NT$12,252 total
includes taxes & fees
Dec 15 - Dec 16
Ocean Key Resort - A Noble House Resort
La Concha Key West
Suite, 1 Bedroom, Non Smoking | Premium bedding, pillowtop beds, minibar, in-room safe
La Concha Key West
4.0 star property
8.0 out of 10, Very Good, (1121)
"I stay here most times that I'm in Key West. Last year during the remodel was a rough time and not a pleasant experience. But this visit, seeing the transformation of the hotel, it is absolutely beautiful. The staff was amazing also. "
The price is NT$8,535
NT$10,576 total
includes taxes & fees
Nov 24 - Nov 25
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, (1000)
"Everything was Amazing,except por one or the staff at the check in,she was really rude, and not friendly at all,the property lovely and clean and perfect "
The price is NT$3,223
NT$5,090 total
includes taxes & fees
Nov 24 - Nov 25
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, (521)
"Lovely rooms and courtyard, and the pool bar is intimate and pleasant with complimentary mimosas etc all day. The staff is friendly and knowledgeable. We would definitely stay again."
The price is NT$11,666
NT$14,586 total
includes taxes & fees
Dec 19 - Dec 20
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 136 places to stay with pools. While you’re visiting, you can explore attractions like Duval Street, and then relax poolside at one of the accommodations in Key West Historic District that travelers 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 136 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 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.