Hotels with a Pool in Key West Historic District, Key West
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Tomorrow night
Check prices in Key West Historic District for tomorrow night, Dec 24 - Dec 25Featured 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
$339 nightly
The price is $381 total per night
$381 total
Jan 12 - Jan 13, 2026
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
Free Cancellation
Reserve now, pay when you stay
$527 nightly
The price is $593 total per night
$593 total
Jan 12 - Jan 13, 2026
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
$339 nightly
The price is $381 total per night
$381 total
Jan 12 - Jan 13, 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
Free Cancellation
Reserve now, pay when you stay
$399 nightly
The price is $449 total per night
$449 total
Jan 5 - Jan 6, 2026
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
Free Cancellation
Reserve now, pay when you stay
$400 nightly
The price is $450 total per night
$450 total
Jan 13 - Jan 14, 2026
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
$589 nightly
The price is $663 total per night
$663 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
$369 nightly
The price is $415 total per night
$415 total
Jan 6 - Jan 7, 2026
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
$219 nightly
The price is $246 total per night
$246 total
Jan 21 - Jan 22, 2026
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
$559 nightly
The price is $629 total per night
$629 total
Jan 4 - Jan 5, 2026
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
$329 nightly
The price is $370 total per night
$370 total
Jan 4 - Jan 5, 2026
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 20 - Jan 21, 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
$271 nightly
The price is $302 total per night
$302 total
Jan 5 - Jan 6, 2026
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
$300 nightly
The price is $338 total per night
$338 total
Jan 8 - Jan 9, 2026
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
$292 nightly
The price is $329 total per night
$329 total
Dec 24 - Dec 25
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
Don't see what you're looking for?
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 | 1,767 hotels |
|---|---|
Lowest Price | $246 |
Highest Price | $663 |
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

La Concha Key West, Autograph Collection
5/5 Excellent
"Very nice staff! Clean hotel! "
A verified traveler from Gatlinburg stayed at La Concha Key West, Autograph Collection
Posted 4 days ago
More to Explore
- Pet-friendly Hotels in Key West
- Visit Ernest Hemingway Home and Museum
- All-inclusive Resorts in Key West
- Resorts in Key West
- Key West vacations
- Romantic Hotels in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels near Duval Street
- Beach Hotels in Key West
- Hotels in Key West
- Condos in Key West
- Flights to Key West
- Car rentals in Key West
- Bed & breakfast in Key West
- Visit Duval Street
- Houseboats in Key West
- Family Hotels in Key West
- Key West vacation rentals


