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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Key West Historic District Hotels with a Pool

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

Courtyard

Douglas House

Douglas House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (282 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
In-room safe, individually decorated, desk, iron/ironing board

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,149 reviews)
"Loved our stay here! "
United States
Brianna
The price is AED 1,027
AED 1,295 total
includes taxes & fees
23 Feb - 24 Feb
Heron House - Adult Only
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 2,035
AED 2,434 total
includes taxes & fees
12 Feb - 13 Feb
Opal Key Resort & Marina, Key West
Courtyard

Duval House

Duval House
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,008 reviews)
"Great place! "
United States
David
The price is AED 1,392
AED 1,645 total
includes taxes & fees
8 Mar - 9 Mar
Duval House
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!
Old Town Key West
9.6 out of 10, Exceptional, (149 reviews)
"Great property. Lots of thoughtful amenities. Management friendly and responsive. "
United States
Diane V.
The price is AED 929
AED 1,686 total
includes taxes & fees
23 Feb - 24 Feb
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
A heated pool

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Old Town Key West
9.8 out of 10, Exceptional, (105 reviews)
"It’s a great location downtown just far enough away from all the noise and commotionWe’re definitely stay here again"
United States
John L.
The price is AED 941
AED 1,842 total
includes taxes & fees
16 Feb - 17 Feb
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Pool

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
Balcony, Pool, & Near Duval - Curry House Room 8
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (337 reviews)
"Great place to stay! "
United States
Alicia
Hyatt Vacation Club at Sunset Harbor, Key West
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
Outdoor pool, a heated pool

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (421 reviews)
"Everything was excellent!"
United States
Susan L.
The price is AED 922
AED 1,589 total
includes taxes & fees
4 Mar - 5 Mar
Steps from Duval, Pool on Site & Bikes Included!
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

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 1 day ago
Pier House Resort & Spa

Explore a world of travel with Expedia

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.