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

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

BBQ/picnic area

Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (8 reviews)
"The room was spotless and very comfortable."
United States
KARLA
Banana's Foster Guesthouse
Courtyard

Duval House

Duval House
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,006 reviews)
"Great place! "
United States
David
The price is AED 1,282
AED 1,521 total
includes taxes & fees
11 Feb - 12 Feb
Duval House
3 outdoor pools, a heated pool, sun loungers

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, (1,026 reviews)
"Staff courteous and room was clean."
United States
Rita
The price is AED 1,190
AED 1,504 total
includes taxes & fees
1 Mar - 2 Mar
NYAH Key West - Adults Only
Courtyard

Douglas House

Douglas House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (280 reviews)
"Great place with a perfect location. "
United States
Brandon
The price is AED 1,304
AED 1,614 total
includes taxes & fees
10 Mar - 11 Mar
Douglas House
View from room

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, (1,049 reviews)
"Great location great staff"
United States
Lori
The price is AED 1,943
AED 2,331 total
includes taxes & fees
11 Feb - 12 Feb
Opal Key Resort & Marina, Key West
A heated pool

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Old Town Key West
9.6 out of 10, Exceptional, (158 reviews)
"Had a wonderful visit and everything was amazing I would highly recommend this place "
United States
Joel
The price is AED 766
AED 1,481 total
includes taxes & fees
17 Feb - 18 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Exterior

The Garden House

The Garden House
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (680 reviews)
"The room was clean. The breakfast was amazing and the Host was available tent I’ve to our needs and a fun person to be around . We slept great and we wanted to know what kind of mattress it was."
United States
Hollie
The price is AED 1,605
AED 1,885 total
includes taxes & fees
24 Feb - 25 Feb
The Garden House
A heated pool

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool
Old Town Key West
9.6 out of 10, Exceptional, (27 reviews)
"The Inn was very well kept, very quiet, comfortable, and clean. We enjoyed our stay very much and it was in a great location. "
United States
Donna H.
The price is AED 1,675
AED 2,632 total
includes taxes & fees
10 Mar - 11 Mar
SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool
A heated pool

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (97 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is AED 1,961
AED 3,040 total
includes taxes & fees
13 Mar - 14 Mar
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Property grounds

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (1,003 reviews)
"Clean room, great breakfast and nice staff"
United States
Tari
The price is AED 1,507
AED 1,695 total
includes taxes & fees
11 Feb - 12 Feb
Orchid Key Inn - 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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Choose what matters most at hotels with a pool in Key West Historic District

Breakfast included
4 stars

Top Key West Historic District Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Everything was incredible! Beautiful resort and everyone was so nice"
Rachel 3-night trip
Posted 17 hours ago
Pier House Resort & Spa

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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 158 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 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. The Reach Key West, Curio Collection by Hilton: Resort steps from South Beach. Provides a private beach, an outdoor pool, and a full-service spa. The Southernmost Inn - Adults Only: Hotel, 1-minute walk from Duval Street. Features daily, 2 outdoor pools, and flat-screen televisions. 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 158 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.