Hotels with a Pool in Key West Historic District, Key West
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Tomorrow night
Check prices in Key West Historic District for tomorrow night, Dec 20 - Dec 21Featured Key West Historic District Hotels with Pool

Silver Palms Inn
830 Truman Ave Key West FL
Free Cancellation
Reserve now, pay when you stay
$298 nightly
The price is $335 total per night
$335 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Guests staying at Silver Palms Inn enjoy an outdoor pool, free WiFi in public areas, and a vending machine. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include an ATM and a TV in a common area.
Pool
Breakfast included

The Southernmost Inn - Adults Only
525 United Street Key West FL
$229 nightly
The price is $258 total per night
$258 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of The Southernmost Inn - Adults Only enjoy features like 2 outdoor pools, a hot tub, and coffee in a common area. Self parking is available for USD 32.25 per day. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this adults-only hotel include a microwave in a common area, express check-out, and a terrace.
Pool
Hot Tub

Pier House Resort & Spa
1 Duval St Key West FL
$425 nightly
The price is $478 total per night
$478 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of Pier House Resort & Spa have access to a private beach, a full-service spa, and an outdoor pool. Self parking is available for USD 40 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a gym, a hot tub, and meeting rooms.
On private beach
Pool

The Cabana Inn Key West - Adults Only
413 Applerouth Lane Key West FL
$280 nightly
The price is $316 total per night
$316 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests of The Cabana Inn Key West - Adults Only enjoy an outdoor pool, a hot tub, and coffee in a common area. Self parking is offered for USD 32.25 per night. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this adults-only guesthouse include express check-out, a terrace, and laundry facilities.
Pool
Hot Tub

Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
$335 nightly
The price is $377 total per night
$377 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Winslow's Bungalows - Key West Historic Inns enjoy features like 3 outdoor pools, free WiFi in public areas, and coffee in a common area. Self parking is available for USD 30 per day. Front-desk staff can assist with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a microwave in a common area, a water dispenser, and a garden.
Pool
Breakfast included

The Marker Key West Harbor Resort
200 William Street Key West FL
$424 nightly
The price is $477 total per night
$477 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at The Marker Key West Harbor Resort enjoy access to 3 outdoor pools, a gym, and free WiFi in public areas. Self parking is available for USD 47.30 per day. The 24-hour front desk has staff standing by to help with luggage storage, tours or tickets, and dry cleaning/laundry. Additional amenities include a 24-hour business center, a meeting room, and a banquet hall.
Pool
Pet friendly

Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
Free Cancellation
Reserve now, pay when you stay
$614 nightly
The price is $691 total per night
$691 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ocean Key Resort - A Noble House Resort features a full-service spa, an outdoor pool, and a 24-hour gym. Valet parking is available for USD 53.75 per day, and there's also limo/town car service. The front desk is staffed 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Other amenities at this spa resort include free WiFi in public areas, conference space, and express check-out.
Pool
Spa

La Concha Key West, Autograph Collection
430 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$329 nightly
The price is $370 total per night
$370 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of La Concha Key West, Autograph Collection have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is available for USD 45 per night. The front desk has multilingual staff standing by 24 hours a day to assist with concierge services and luggage storage. Additional amenities include meeting rooms, conference space, and express check-out.
Pool
Pet friendly

NYAH Key West - Adults Only
420 Margaret Street Key West FL
$171 nightly
The price is $193 total per night
$193 total
Dec 22 - Dec 23
Total with taxes and fees
3 outdoor pools, a rooftop terrace, and a hot tub are featured at NYAH Key West - Adults Only. The front desk has multilingual staff standing by 24 hours a day to assist with luggage storage and concierge services. Other amenities at this adults-only guesthouse include coffee/tea in a common area, a terrace, and a water dispenser.
Pool
Hot Tub

H2O Suites - Adults Only
1212 Simonton Street Key West FL
$499 nightly
The price is $561 total per night
$561 total
Dec 21 - Dec 22
Total with taxes and fees
At H2O Suites - Adults Only, guests enjoy features like an outdoor pool, a gym, and a rooftop terrace. Self parking is offered for USD 45.00 per day. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, luggage storage, and concierge services. Other amenities at this adults-only hotel include free newspapers, a terrace, and laundry facilities.
Pool
Free WiFi

Heron House - Adult Only
512 Simonton St Key West FL
$210 nightly
The price is $236 total per night
$236 total
Dec 22 - Dec 23
Total with taxes and fees
Heron House - Adult Only offers an outdoor pool, a rooftop terrace, and free WiFi in public areas. Front-desk staff can assist with tours/tickets and luggage storage. Other amenities at this adults-only bed & breakfast include free newspapers and a garden.
Pool
Breakfast included

Eden House
1015 Fleming St Key West FL
$448 nightly
The price is $504 total per night
$504 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Eden House offers an outdoor pool, free WiFi in public areas, and a hot tub. There's discounted offsite parking and a ferry terminal shuttle. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include coffee/tea in a common area, a refrigerator in a common area, and a computer station.
Pool
Hot Tub

Duval House
815 Duval St Key West FL
$220 nightly
The price is $244 total per night
$244 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of Duval House enjoy features like microwave in a common area, express check-in and express check-out. If you drive, self parking is USD 32.25 per night, and there's also an area shuttle. The front desk has multilingual staff that can help with tours or tickets, securing valuables, and luggage storage. Other amenities at this adults-only bed & breakfast include free newspapers, a terrace, and wedding services.
Air conditioning
Parking available

Paradise Inn Key West - Adults Only
819 Simonton Street Key West FL
$239 nightly
The price is $269 total per night
$269 total
Dec 23 - Dec 24
Total with taxes and fees
Paradise Inn Key West - Adults Only features an outdoor pool, a hot tub, and coffee in a common area. Self parking is offered for USD 32.25 per night. The front desk has multilingual staff that can help with concierge services, securing valuables, and luggage storage. Other amenities at this adults-only hotel include a terrace, a TV in a common area, and a garden.
Pool
Hot Tub

Heron House Court - Adult Only
412 Frances St Key West FL
$312 nightly
The price is $351 total per night
$351 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Heron House Court - Adult Only, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this adults-only guesthouse include coffee/tea in a common area, a terrace, and a garden.
Pool
Free WiFi
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See all available properties in Key West Historic District
View all propertiesLowest 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.
Key West Historic District hotels essential information
Accommodation | 1,769 hotels |
|---|---|
Lowest Price | $193 |
Highest Price | $691 |
Popular hotels | Silver Palms Inn, The Southernmost Inn - Adults Only, Pier House Resort & Spa, The Cabana Inn Key West - Adults Only, Winslow's Bungalows - Key West Historic Inns, The Marker Key West Harbor Resort, Ocean Key Resort - A Noble House Resort, La Concha Key West, Autograph Collection, NYAH Key West - Adults Only, H2O Suites - Adults Only, Heron House - Adult Only, Eden House, Duval House, Paradise Inn Key West - Adults Only, Heron House Court - Adult Only |
Recent Hotels with Pool Reviews

Hyatt Centric Key West Resort and Spa
5/5 Excellent
"Staff was courteous and the location is perfect for a weekend in Key West."
A verified traveler stayed at Hyatt Centric Key West Resort and Spa
Posted 4 days ago
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