Key West Historic District Hotel with Pool

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Check availability on Key West Historic District Hotel with Pool

Top Key West Historic District Hotel with Pool

Silver Palms Inn
Outdoor pool

Silver Palms Inn

3.5 star property
9.2 out of 10, Wonderful, (1008)
"Great customer service"
The price is HK$2,234
HK$3,038 total
includes taxes & fees
4 Feb - 5 Feb
Silver Palms Inn
The Southernmost Inn - Adults Only
Courtyard

The Southernmost Inn - Adults Only

3.0 star property
8.0 out of 10, Very good, (1008)
"This was our fourth year that we stayed at Southernmost Inn. We love the location, the laid back atmosphere, the charm of the buildings and property. Tamesha and Kia at the front office are wonderful and so helpful, and the Inn staff are very accommodating and friendly. The accommodations are lovely and comfortable, the property is very well maintained. We plan to return again in January 2026 for our annual vacation. "
The price is HK$2,562
HK$3,232 total
includes taxes & fees
29 Jan - 30 Jan
The Southernmost Inn - Adults Only
Pier House Resort & Spa
View from room

Pier House Resort & Spa

4.0 star property
9.0 out of 10, Wonderful, (1004)
" Very nice but paying for location, that is fine . Beach was very nice relaxing and clean property was clean . Weather gorgeous, room was loud we were on ground floor . Air conditioning was to cold when running but to warm when off but this is common . Overall very nice hotel !!"
The price is HK$5,676
HK$6,876 total
includes taxes & fees
29 Jan - 30 Jan
Pier House Resort & Spa
The Cabana Inn Key West - Adults Only
Courtyard

The Cabana Inn Key West - Adults Only

3.0 star property
8.8 out of 10, Excellent, (1002)
"Solid stay "
The price is HK$4,975
HK$5,947 total
includes taxes & fees
3 Feb - 4 Feb
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, pool loungers

Winslow's Bungalows - Key West Historic Inns

4.0 star property
9.0 out of 10, Wonderful, (1000)
"This is a very interesting property. We stayed in one of the bungalows though there are other types of rooms available. It is an old property, but recently refurbished/renovated. The room was small but well appointed and had a nice bathroom with a tiled walk-in shower. There is a nice full service outdoor bar adjacent to the kitchen area. A very nice breakfast is included with the reservation. There is free WiFi which is pretty good. The biggest downside to Winslow’s is the satellite tv. There...
The price is HK$3,106
HK$3,819 total
includes taxes & fees
28 Jan - 29 Jan
Winslow's Bungalows - Key West Historic Inns
The Marker Key West Harbor Resort
3 outdoor pools, pool umbrellas, pool loungers

The Marker Key West Harbor Resort

4.0 star property
8.8 out of 10, Excellent, (1004)
"Very nice stay at the Marker! Room, pool, bar and employees were all great, would definitely stay there again!"
The price is HK$3,637
HK$4,564 total
includes taxes & fees
28 Jan - 29 Jan
The Marker Key West Harbor Resort
Ocean Key Resort - A Noble House Resort
Outdoor pool, pool loungers

Ocean Key Resort - A Noble House Resort

4.0 star property
9.2 out of 10, Wonderful, (1003)
"This was my 1st time at this property and I can’t say enough good things. Our room had a balcony facing the port so we got to see the cruise ships coming and going. We also were able to see every sunset without leaving our room. The property is very clean and well maintained. We had an excellent breakfast at the Hot Tin Roof restaurant overlooking the pool, ocean and Sun Set Key. We will definitely be back. "
The price is HK$4,424
HK$5,503 total
includes taxes & fees
26 Jan - 27 Jan
Ocean Key Resort - A Noble House Resort
La Concha Key West, Autograph Collection
Exterior

La Concha Key West, Autograph Collection

4.0 star property
8.0 out of 10, Very good, (1091)
"Great hotel, excellent location, close to everything."
The price is HK$3,260
HK$3,901 total
includes taxes & fees
27 Jan - 28 Jan
La Concha Key West, Autograph Collection
NYAH Key West - Adults Only
Outdoor spa tub

NYAH Key West - Adults Only

3.0 star property
7.6 out of 10, Good, (1003)
"Was as expected and gave us an extra night in Key West. "
The price is HK$1,418
HK$1,945 total
includes taxes & fees
27 Jan - 28 Jan
NYAH Key West - Adults Only
H2O Suites - Adults Only
View from room

H2O Suites - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (526)
"Rooms are as they appear online. If you can’t do stairs please let them know in advance as our room could only be accessed with stairs. When it rained (and it did!) those stairs were very slippery. Definitely a safety hazzard in my opinion. "
The price is HK$4,664
HK$5,597 total
includes taxes & fees
2 Feb - 3 Feb
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 relaxing by the pool is your idea of a great getaway, you might want to think about Key West Historic District, which offers 134 places to stay with pools. While you’re here, you can explore attractions such as Duval Street and Saint Mary Star of the Sea, and then relax and unwind poolside at one of the accommodation options in Key West Historic District that guests like for their pools.
What are some accommodation options with pools in Key West Historic District?
Southernmost Beach Resort: Hotel steps from Southernmost Point. Features 2 pool bars, 3 outdoor swimming pools and a full-service spa. Winslow’s Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Offers daily, 3 outdoor swimming 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, 2-minute walk from Florida Keys Beaches. 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 should I expect to find in Key West Historic District?
Expedia’s 134 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?
Make a point to visit attractions such as South Beach and Mel Fisher Maritime Museum. During your stay, visit sights such as Duval Street, Saint Mary Star of the Sea and Ernest Hemingway Home and Museum. Key West Historic District appeals to visitors with its bar scene and great live music scene.