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

Courtyard

Douglas House

Douglas House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (289 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
Exterior

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.4 out of 10, Very Good, (552 reviews)
"Beautiful beach- gorgeous hotel-top level service - love everything about it!"
United States
Debbie
The price is AED 2,347
AED 2,888 total
includes taxes & fees
25 Feb - 26 Feb
Casa Marina Key West, Curio Collection by Hilton
Courtyard

Duval House

Duval House
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,009 reviews)
"Great place! "
United States
David
The price is AED 1,392
AED 1,645 total
includes taxes & fees
5 Mar - 6 Mar
Duval House
Outdoor pool, pool umbrellas, sun loungers

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1,011 reviews)
"Hotel was very nice in all respects, but its location on the beach was the best."
United States
Stephen
The price is AED 2,107
AED 2,618 total
includes taxes & fees
8 Mar - 9 Mar
The Reach Key West, Curio Collection by Hilton
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, (1,005 reviews)
"Nice location and nice Hostel! Would go again. "
United States
Christopher
The price is AED 1,190
AED 1,504 total
includes taxes & fees
1 Mar - 2 Mar
NYAH Key West - Adults Only
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
Porch

Heron House Court - Adult Only

Heron House Court - Adult Only
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1,006 reviews)
"Nice room, comfortable bed, friendly staff"
United States
Ben
The price is AED 1,121
AED 1,403 total
includes taxes & fees
3 Mar - 4 Mar
Heron House Court - Adult Only
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)
"Very quaint room and the location was perfect which allowed us to walk anywhere we wanted to venture. "
United States
Donald R.
The price is AED 1,140
AED 2,092 total
includes taxes & fees
28 Feb - 1 Mar
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
A heated pool

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Old Town Key West
9.8 out of 10, Exceptional, (138 reviews)
"Quaint and quiet, clean and lovely place. Would recommend a key code lock for guests only on front door and gates for security but we had no issues. Pool heated, amenities provided as described. "
United States
Michelle
The price is AED 782
AED 1,499 total
includes taxes & fees
3 Mar - 4 Mar
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
A heated pool

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

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (120 reviews)
"we had a wonderful room with a great location. It was too cold to use the pool, but it looked very inviting. Would definitely stay again."
United States
Richard
The price is AED 951
AED 1,760 total
includes taxes & fees
25 Feb - 26 Feb
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
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

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Very convenient location "
Leyany 1-night trip
Posted 8 hours ago
Southwinds Motel

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 167 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. Hyatt Centric Key West Resort and Spa: Resort, 3-minute walk from Duval Street. Features a full-service spa, a pool, and a snack bar/deli. Opal Key Resort & Marina, Key West: Hotel steps from Mallory Square. Offers 3 bars, an outdoor pool, and spa services.
How many hotels with pools will I find in Key West Historic District?
Expedia's 167 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.