Key West Hotels with Pool
Check availability on Key West Hotels with Pool
Featured Key West Hotels with Pool

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
The price is €330 per night
€330
21 Dec - 22 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the pool at Southernmost Beach Resort and Guesthouses. During your stay, you're just a quick walk from Duval Street. Features include 3 outdoor pools, 2 poolside bars and a full-service spa.
Pool
Spa

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is €272 per night
€272
21 Dec - 22 Dec
includes taxes & fees
Our customers tell us they can't get enough of Blue Flamingo Resort Key West's great location. During your stay, you'll be within walking distance of Regal Key West. Enjoy features like free WiFi in public areas and a free area shuttle, plus 2 outdoor pools. This property offers pet-friendly amenities, such as an off-lead area.
Pool
Hot tub

Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
The price is €267 per night
€267
4 Jan - 5 Jan 2026
includes taxes & fees
The free breakfast at Hampton Inn Key West FL gets high marks from our customers. During your stay, you're just a quick walk from Fort East Martello Museum and Gallery. Free WiFi in public areas, an outdoor pool and a restaurant are available.
Pool
Breakfast included

Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
The price is €261 per night
€261
13 Jan - 14 Jan 2026
includes taxes & fees
Our customers tell us they can't get enough of Parrot Key Hotel & Villas's great location. During your stay, you'll be within walking distance of Regal Key West. Enjoy features like free WiFi in public areas and a free area shuttle, plus 4 outdoor pools.
Pool
Pet-friendly

Silver Palms Inn
830 Truman Ave Key West FL
The price is €256 per night
€256
22 Dec - 23 Dec
includes taxes & fees
The free breakfast at Silver Palms Inn gets high marks from our customers. During your stay, you're just a quick walk from Duval Street. Features include free WiFi in public areas, plus an outdoor pool and concierge services.
Pool
Breakfast included

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
During your stay at Margaritaville Beach House Key West, you'll be within walking distance of Florida Keys Beaches. Enjoy features like free self-parking, plus 2 restaurants and an outdoor pool.
Pool
Hot tub

Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd Key West FL
The price is €234 per night
€234
21 Dec - 22 Dec
includes taxes & fees
The free breakfast at Fairfield Inn and Suites by Marriott Key West gets high marks from our customers. During your stay, you'll be within walking distance of Florida Keys Beaches. Enjoy features like free WiFi in public areas, plus an outdoor pool and a restaurant.
Pool
Breakfast included

The Southernmost Inn - Adults Only
525 United Street Key West FL
The price is €220 per night
€220
21 Dec - 22 Dec
includes taxes & fees
The free breakfast at The Southernmost Inn - Adults Only gets good marks from our customers. During your stay, you're just a quick walk from Duval Street. Enjoy features like a free manager's reception, plus 2 outdoor pools and a coffee shop/cafe.
Pool
Hot tub

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
The price is €295 per night
€295
11 Jan - 12 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the pool at Oceans Edge Key West Resort, Hotel & Marina. During your stay, you're just a quick walk from Stock Island Yacht Club & Marina. Enjoy features like free WiFi in public areas, plus 6 outdoor pools and a restaurant.

Fairfield Inn & Suites by Marriott Key West at the Keys Collection
3852 North Roosevelt Boulevard Key West FL
The price is €255 per night
€255
4 Jan - 5 Jan 2026
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at Fairfield by Marriott Inn & Suites Key West at The Keys Collection. During your stay, you'll be within walking distance of Key West Tropical Forest and Botanical Garden. Features include free WiFi in public areas, plus an outdoor pool and a gym.
Pool
Breakfast included

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is €259 per night
€259
4 Jan - 5 Jan 2026
includes taxes & fees
Our customers tell us they can't get enough of DoubleTree Resort by Hilton Grand Key - Key West's great location. During your stay, you'll be within walking distance of Fort East Martello Museum and Gallery. Free WiFi in public areas, a free round-trip airport shuttle and a free beach shuttle are available.
Pool
Free airport shuttle

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
The price is €204 per night
€204
21 Dec - 22 Dec
includes taxes & fees
The free breakfast at Ibis Bay Beach Resort gets good marks from our customers. During your stay, you're just a quick walk from Regal Key West. Enjoy features like free WiFi in public areas, plus an outdoor pool and a restaurant.

The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
The price is €366 per night
€366
13 Jan - 14 Jan 2026
includes taxes & fees
Our customers tell us they can't get enough of The Reach Key West, Curio Collection by Hilton's great beach location. During your stay, you're just a quick walk from Duval Street. You'll find features such as a full-service spa, an outdoor pool and a restaurant.

Pier House Resort & Spa
1 Duval St Key West FL
The price is €423 per night
€423
23 Dec - 24 Dec
includes taxes & fees
Our customers tell us they can't get enough of Pier House Resort & Spa's great beach location. During your stay, you're just a quick walk from Duval Street. 2 bars, a full-service spa and an outdoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.
On private beach
Pool

The Cabana Inn Key West - Adults Only
413 Applerouth Lane Key West FL
The free breakfast at The Cabana Inn Key West - Adults Only gets high marks from our customers. During your stay, you're just a quick walk from Duval Street. You'll find features such as an outdoor pool, a snack bar/deli and 1 hot tub.
Pool
Hot tub
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.
Key West hotels essential information
Accommodation | 2,775 hotels |
|---|---|
Lowest Price | €204 |
Highest Price | €423 |
Popular hotels | Southernmost Beach Resort and Guesthouses, Blue Flamingo Resort Key West, Hampton Inn Key West FL, Parrot Key Hotel & Villas, Silver Palms Inn, Margaritaville Beach House Key West, Fairfield Inn and Suites by Marriott Key West, The Southernmost Inn - Adults Only, Oceans Edge Key West Resort, Hotel & Marina, Fairfield Inn & Suites by Marriott Key West at the Keys Collection, DoubleTree Resort by Hilton Grand Key - Key West, Ibis Bay Beach Resort, The Reach Key West, Curio Collection by Hilton, Pier House Resort & Spa, The Cabana Inn Key West - Adults Only |
Recent Key West hotel reviews by travellers like youebookers verified reviews

Hyatt Centric Key West Resort and Spa
5/5 Excellent
"Room with a view clean and a great location "
A verified traveller stayed at Hyatt Centric Key West Resort and Spa
Posted 4 days ago
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