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

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Check availability on Key West Historic District Hotels with a Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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

Outdoor spa tub
NYAH Key West - Adults Only

NYAH Key West - Adults Only

NYAH Key West - Adults Only
3.0 star property
Key West Historic District
8.0 out of 10, Very Good, (1004)
"Great stay"
United States
Venkata Durga Phanindra Reddy
The price is ￥29,301
￥40,008 total
includes taxes & fees
Jan 21 - Jan 22, 2026
NYAH Key West - Adults Only
3 outdoor pools, pool umbrellas, sun loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
4.0 star property
Old Town Key West
8.8 out of 10, Excellent, (2959)
"Wonderful stay!"
United States
Elisa
The price is ￥46,228
￥63,457 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Southernmost Beach Resort and Guesthouses
Courtyard
Duval House

Duval House

Duval House
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1005)
"Great place! "
United States
David
The price is ￥38,986
￥47,225 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Duval House
Outdoor pool, pool umbrellas, sun loungers
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Old Town Key West
9.2 out of 10, Wonderful, (1006)
"Great stay! Close to Duval Street."
United States
Manuel
Paradise Inn Key West - Adults Only
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers
Heron House Court - Adult Only

Heron House Court - Adult Only

Heron House Court - Adult Only
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1003)
"Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. "
United States
Chandler
The price is ￥29,451
￥38,657 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Heron House Court - Adult Only
A heated pool
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Old Town Key West
9.6 out of 10, Exceptional, (144)
"Great property. Lots of thoughtful amenities. Management friendly and responsive. "
United States
Diane V.
The price is ￥19,258
￥46,033 total
includes taxes & fees
Jan 8 - Jan 9, 2026
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Exterior
Heron House - Adult Only

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (1140)
"Clean room and staff was great"
United States
Paul
The price is ￥33,694
￥43,551 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Heron House - Adult Only
Herlihy, Ground Floor, Poolside | Individually decorated, individually furnished, iron/ironing board
Authors of Key West Guest House

Authors of Key West Guest House

Authors of Key West Guest House
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1005)
"Everyone was awesome and the rooms and pool was great also"
United States
Mary
The price is ￥32,269
￥36,304 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Authors of Key West Guest House
Outdoor pool
Silver Palms Inn

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1007)
"everything is great, love the room, the location, and the quiet ac"
United States
Qi
The price is ￥37,906
￥53,213 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Silver Palms Inn
View from room
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1029)
"Our stay was great!"
United States
Richard
The price is ￥65,603
￥79,970 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Opal Key Resort & Marina, Key West
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

Top Key West Historic District Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"The location is great, with lots of courtyard and pool space to lounge in around the property. We loved being able to rent bikes on site, as well as the included breakfast and happy hours each day. "
Marsha 4-night trip
Posted 1 day ago
The Southernmost Inn - Adults Only

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 155 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 and Guesthouses: Hotel steps from Southernmost Point. Features 2 pool bars, 3 outdoor pools, and a full-service spa. 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. Winslow's Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Provides daily, 3 outdoor pools, and complimentary wireless internet access. 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, 3-minute walk from Duval Street. Offers a full-service spa, a pool, and a snack bar/deli.
How many hotels with pools will I find in Key West Historic District?
Expedia's 155 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.