Find hotels with pools in Key West Historic District, Key West from $136

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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.

Deluxe Suite, 1 King Bed, Private Pool | View from 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 $459
$561 total
includes taxes & fees
Jun 19 - Jun 20
H2O Suites - Adults Only
View from property
Duval House
3.0 star property
9.4 out of 10, Exceptional, (1001)
"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 $159
$200 total
includes taxes & fees
May 29 - May 30
Duval House
Outdoor pool
Silver Palms Inn
3.5 star property
9.2 out of 10, Wonderful, (1005)
"Very loud air conditioners in room. "
The price is $148
$222 total
includes taxes & fees
May 27 - May 28
Silver Palms Inn
Outdoor pool, sun loungers
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 $353
$461 total
includes taxes & fees
Jun 16 - Jun 17
Ocean Key Resort - A Noble House Resort
Cottage, 2 Bedrooms (Royal Poinciana) | Terrace/patio
Paradise Inn Key West - Adults Only
3.5 star property
9.2 out of 10, Wonderful, (1000)
"The pool is was quiet and beautiful. Very relaxing. Our room was clean but the toilet kept not filling up with water. Also one staff member acted very annoyed by any request we had."
The price is $269
$348 total
includes taxes & fees
Jun 19 - Jun 20
Paradise Inn Key West - Adults Only
Free daily continental breakfast
Heron House - Adult Only
3.5 star property
9.0 out of 10, Wonderful, (1065)
"This place was amazing. So many nice people. Clean and pleasant. Highly recommend this place. "
The price is $161
$206 total
includes taxes & fees
May 27 - May 28
Heron House - Adult Only
Queen Island Room | Down comforters, pillowtop beds, in-room safe, iron/ironing board
Eden House
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Excellent hotel, extremely friendly staff, all the amenities we were looking for, 3 minute nice walk to Duval st. Highly recommend!!"
The price is $256
$323 total
includes taxes & fees
Jun 3 - Jun 4
Eden House
Suite (Dockside) | Balcony
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 $499
$622 total
includes taxes & fees
May 23 - May 24
Pier House Resort & Spa
Courtyard
The Cabana Inn Key West - Adults Only
3.0 star property
8.8 out of 10, Excellent, (1004)
"It really was a lovely property. Parking isn't the best, we had to park next door. Happy hour is wine only and some beer would be nice. The beds were very comfortable. I would stay here again"
The price is $289
$370 total
includes taxes & fees
May 28 - May 29
The Cabana Inn Key West - Adults Only
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns
4.0 star property
8.8 out of 10, Excellent, (715)
"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 $310
$390 total
includes taxes & fees
Jun 6 - Jun 7
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.

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Key West Historic District Hotels with a Pool information

 

Hotels with a Pool in Key West Historic District

60

Highest price
$499
Cheapest price
$136
Number of guest reviews
9,465
Total number of hotels in Key West Historic District
1,735

 

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 239 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: 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. NYAH Key West - Adults Only: Guesthouse, 7-minute walk from Duval Street. Provides a rooftop terrace, 3 outdoor pools, and a snack bar/deli. Pier House Resort & Spa: Resort steps from Mallory Square. Features a private beach, an outdoor pool, and a full-service spa. 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 239 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

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

5/5 Excellent
"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 at no extra charge. Another great perk is the onsite bar. It was nice to be able to get an afternoon beverage right there where we were staying. The staff were wonderful, and super friendly. The room was super clean, the beds were super comfy, and we were super comfortable during our stay."
A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns
Posted 23 hours ago
Winslow's Bungalows - Key West Historic Inns