The Best Hotels with a Pool in Key West Historic District, FL from ￥24,799 in 2026

Q: 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. The Reach Key West, Curio Collection by Hilton : Resort steps from South Beach. Offers a private beach, an outdoor pool, and a full-service spa. Hyatt Centric Key West Resort and Spa : Resort, 1-minute walk from Florida Keys Beaches. Provides a full-service spa, a pool, and a snack bar/deli. Winslow's Bungalows - Key West Historic Inns : Hotel, 5-minute walk from Duval Street. Features complimentary wireless internet access, 3 outdoor pools, and LED televisions. Opal Key Resort & Marina, Key West : Hotel steps from Mallory Square. Offers 3 bars, an outdoor pool, and spa services.

A two-story house with green shutters and a wooden balcony.

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

1. Island City House Hotel

Key West Historic District

￥28,285 total

includes taxes & fees

Aug 17 - Aug 18

2. The Marquesa Hotel

Old Town Key West

￥48,950 total

includes taxes & fees

Aug 23 - Aug 24

Outdoor pool, pool umbrellas, sun loungers

3. Almond Tree Inn Hotel - Adults Only

Old Town Key West

￥34,487 total

includes taxes & fees

Aug 11 - Aug 12

4. Santa Maria Suites

Old Town Key West

￥56,584 total

includes taxes & fees

Aug 23 - Aug 24

Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

5. Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Take a dip in Key West's serene outdoor pool oasis, where relaxation meets historic charm just steps from Duval Street.

￥42,573 total

includes taxes & fees

Aug 9 - Aug 10

6. Paradise Inn Key West - Adults Only

Old Town Key West

Dreamy poolside escape awaits in this Key West oasis with outdoor pool and hot tub paradise.

￥25,759 total

includes taxes & fees

Aug 25 - Aug 26

7. Silver Palms Inn & Historic Homes

Old Town Key West

Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.

￥24,799 total

includes taxes & fees

Aug 19 - Aug 20

8. Opal Key Resort & Marina, Key West

Old Town Key West

￥52,151 total

includes taxes & fees

Aug 11 - Aug 12

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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

The Marker Key West Harbor Resort

10/10 Excellent

"Lovely room with comfortable beds. The location right on the Harborwalk was perfect."

Ocean Key Resort - A Noble House Resort

8/10 Good

"We had a nice stay at Ocean Key Resort. The location is great! There was a lot of noise from the balcony from Pier House Hotel AC units, but you could watch the sunsets with the band playing at the sunset pier below drowning out the AC noise. Overall it’s a nice resort! I would recommend staying here."

The Palms Hotel

10/10 Excellent

"This was a very lovely hotel and I’m glad I chose it. I had a really nice room to 214 A, and it overlooked the pool. The room was very spacious and the bathroom was a nice size except for the shower stall itself, which was fairly small. Everything was incredibly clean and the staff did a really great job."

Duval House

8/10 Good

"Wonderful property, peaceful and clean with amazing in town location. Room was nice. Check- in and out were smooth and easy, with very kind staff. Parking is an issue and extra cost, as we are sure is with most old town properties, information about other options for parking would help on the site etc. Breakfast was good, not great (parfaits were nice, hard boiled eggs and waffles are nice choices and OK), staff were kind and helpful. If high traffic there is a bit of a wait for the waffles."

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 186 places to stay with pools. While you're visiting, you can explore attractions like Duval Street and Florida Keys Beaches, and then relax poolside at one of the accommodations in Key West Historic District that guests 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. The Reach Key West, Curio Collection by Hilton: Resort steps from South Beach. Offers a private beach, an outdoor pool, and a full-service spa. Hyatt Centric Key West Resort and Spa: Resort, 1-minute walk from Florida Keys Beaches. Provides a full-service spa, a pool, and a snack bar/deli. Winslow's Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Features complimentary wireless internet access, 3 outdoor pools, and LED televisions. 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 186 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 and Florida Keys Beaches while you're in Key West Historic District. The picturesque setting of Key West Butterfly and Nature Conservatory and South Beach showcase the area's natural beauty. Key West Historic District appeals to visitors with its bar scene and great live music scene.

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