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

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Pick from 60 Key West Historic District Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Room
H2O Suites - Adults Only
3.5 star property
9.8 out of 10, Exceptional, (481)
"We will definitely be back to this hotel. Amazing staff, service and little attention to details. Special thanks to Angie at the bar, your were so sweet and made our afternoon at the pool enjoyable. "
The price is SAR 1,721
SAR 2,067 total
includes taxes & fees
27 Jum. I - 28 Jum. I
H2O Suites - Adults Only
Courtyard
Duval House
3.0 star property
9.4 out of 10, Exceptional, (1002)
"I enjoyed my stay at the Duval Housr. It gave me the feeling of being in old Florida, but with modern amenities. It was centrally located and is convenient to many of the old town places of interest. I also liked the continental breakfast with the vanilla yogurt, fruit and granola that was put together by the staff. The waffles, made on request were also wonderful. The property is picturesque and had a nostalgic feel. Overall, my stay was delightful!!!"
The price is SAR 596
SAR 752 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Duval House
Outdoor pool
Silver Palms Inn
3.5 star property
9.2 out of 10, Wonderful, (1006)
"Very loud air conditioners in room. "
The price is SAR 615
SAR 903 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Silver Palms Inn
Exterior
Ocean Key Resort - A Noble House Resort
4.0 star property
9.2 out of 10, Wonderful, (1003)
"All of it! We loved the location! We loved the staff! Thank you"
The price is SAR 1,384
SAR 1,793 total
includes taxes & fees
16 Jum. II - 17 Jum. II
Ocean Key Resort - A Noble House Resort
Outdoor pool
Paradise Inn Key West - Adults Only
3.5 star property
9.2 out of 10, Wonderful, (1000)
"BEAUTIFUL ROOM"
The price is SAR 874
SAR 1,133 total
includes taxes & fees
30 Jum. I - 31 Jum. I
Paradise Inn Key West - Adults Only
View from room
Heron House - Adult Only
3.5 star property
9.0 out of 10, Wonderful, (1067)
"Staffs were friendly and it was quiet. Close to shopping and dining. Walkable distance to two beaches."
The price is SAR 571
SAR 723 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Heron House - Adult Only
Pool
Eden House
3.5 star property
9.0 out of 10, Wonderful, (1003)
"Excellent hotel, extremely friendly staff, all the amenities we were looking for, 3 minute nice walk to Duval st. Highly recommend!!"
The price is SAR 1,061
SAR 1,274 total
includes taxes & fees
23 Jum. II - 24 Jum. II
Eden House
Beach
Pier House Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (1002)
"Great place and location. Can walk to the bars and restaurants. Highly recommended."
The price is SAR 1,872
SAR 2,275 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Pier House Resort & Spa
Exterior
The Cabana Inn Key West - Adults Only
3.0 star property
8.8 out of 10, Excellent, (1005)
"Amazing! Cute little inn that was clean, in a great location, room was amazing, and staff was extraordinary! "
The price is SAR 896
SAR 1,156 total
includes taxes & fees
28 Jum. I - 29 Jum. I
The Cabana Inn Key West - Adults Only
Exterior
Winslow's Bungalows - Key West Historic Inns
4.0 star property
8.8 out of 10, Excellent, (717)
"Winslow's Bungalows were a much needed respite from the "real world." I love the history of the inns, and this is what originally made me book this location. The location is very walkable, and we walked down the street to a local bike rental to rent bikes. We were then able to bike all over the historic district. The reviews showed me that Winslow's had an amazing continental breakfast, and this was very much the truth. This was absolutely the best breakfast that I have had that was provided...
The price is SAR 996
SAR 1,252 total
includes taxes & fees
23 Jum. II - 24 Jum. II
Winslow's Bungalows - Key West Historic Inns
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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.

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 235 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.
How many hotels with pools will I find in Key West Historic District?
Expedia’s 235 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.

Recent reviews of Key West Historic District hotels
Expedia verified reviews

Southwinds Motel

Southwinds Motel

5/5 Excellent
"The live music was wonderful and the Southwinds Motel is within walking distance to all the Key West excitment!"
A verified traveler stayed at Southwinds Motel
Posted 15 hours ago
Southwinds Motel