A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Key West Hotels with Swimming Pools

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Key West hotels with a pool

Outdoor pool, pool umbrellas, pool loungers

Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1,420 reviews)
  • cleanliness
    Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
The price is RM895
RM1,006 total
includes taxes & fees
4 Aug - 5 Aug
Hampton Inn Key West FL
Outdoor pool

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,175 reviews)
  • cleanliness
    Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
The price is RM1,451
RM1,817 total
includes taxes & fees
27 Jul - 28 Jul
Hyatt Vacation Club at Windward Pointe, Key West
Exterior detail

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,136 reviews)
  • cleanliness
    Bask in tropical bliss with a dip in the outdoor pool and hot tub near Smathers Beach.
The price is RM1,258
RM1,598 total
includes taxes & fees
20 Jul - 21 Jul
Hyatt Vacation Club at Beach House, Key West
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

The Laureate Key West

The Laureate Key West
3.5 star property
New Town
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Splash into relaxation with indoor and outdoor pools surrounded by plush loungers and umbrellas at this waterfront retreat.
The price is RM647
RM843 total
includes taxes & fees
13 Jul - 14 Jul
The Laureate Key West
Outdoor pool, pool umbrellas, pool loungers

Pier House Resort & Spa

Pier House Resort & Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1,219 reviews)
The price is RM1,184
RM1,617 total
includes taxes & fees
14 Jul - 15 Jul
Pier House Resort & Spa
Exterior

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1,006 reviews)
The price is RM969
RM1,374 total
includes taxes & fees
13 Jul - 14 Jul
Hyatt Centric Key West Resort and Spa
Poolside bar

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.4 out of 10, Very good, (2,499 reviews)
  • cleanliness
    Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
The price is RM509
RM802 total
includes taxes & fees
14 Jul - 15 Jul
Blue Flamingo Resort Key West
Outdoor pool

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
New Town
8.6 out of 10, Excellent, (1,045 reviews)
  • cleanliness
    Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.
The price is RM547
RM731 total
includes taxes & fees
15 Jul - 16 Jul
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
2 outdoor pools, pool loungers

Santa Maria Suites

Santa Maria Suites
4.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,005 reviews)
The price is RM1,258
RM1,690 total
includes taxes & fees
12 Jul - 13 Jul
Santa Maria Suites
Outdoor pool, pool umbrellas, pool loungers

Ibis Bay Beach Resort

Ibis Bay Beach Resort
2.5 star property
Northside Resort
8.2 out of 10, Very good, (2,283 reviews)
  • cleanliness
    Splash into paradise at this Art Deco hotel with a poolside bar and marina access.
The price is RM380
RM559 total
includes taxes & fees
8 Jul - 9 Jul
Ibis Bay Beach Resort
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.
View all properties

Choose what matters most at hotels with a pool in Key West

Breakfast included
Hot tub

Hotels with pools and free breakfast in Key West

Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Key West FL

Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1420)
The price is RM895
RM1,006 total
includes taxes & fees
4 Aug - 5 Aug
Hampton Inn Key West FL
View all properties

Hotels with pools and hot tubs in Key West

Property grounds
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1175)
The price is RM1,451
RM1,817 total
includes taxes & fees
27 Jul - 28 Jul
Hyatt Vacation Club at Windward Pointe, Key West
View all properties

4-star hotels with pools in Key West

4 outdoor pools, pool umbrellas, pool loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
4.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1423)
The price is RM585
RM893 total
includes taxes & fees
8 Jul - 9 Jul
Parrot Key Hotel & Villas
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.
View all properties

Top Key West Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The hotel was very nice and the room was great. Unfortunately the sargassum was so intense that the rotting smell was not favorable."
Magdalena 1-night trip
Posted 1 hour ago
Casa Marina Key West, Curio Collection by Hilton

Frequently asked questions

What's it like visiting Key West?
If relaxing by the pool is your idea of the perfect getaway, you might want to think about Key West, which has 325 places to stay with pools. During your trip, you can explore attractions such as Duval Street and Mallory Square, and then take it easy poolside at one of the accommodation options in Key West that guests like for their pools.
What are some hotels with pools in Key West?
Blue Flamingo Resort Key West: Hotel located near Florida Keys Beaches. Features 2 restaurants, 2 outdoor swimming pools and 2 pool bars. Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Offers 2 pool bars, 3 outdoor swimming pools and a full-service spa. Hilton Garden Inn Key West / The Keys Collection: Hotel located near Florida Keys Beaches. Provides 2 restaurants, a pool and complimentary high-speed (wired) Internet access. The Reach Key West, Curio Collection by Hilton: Resort steps from South Beach. Features a private beach, an outdoor pool and a full-service spa. Parrot Key Hotel & Villas: Hotel located near Florida Keys Beaches. Offers a beach shuttle, 4 outdoor swimming pools and complimentary wireless Internet access.
How many hotels with pools will I find in Key West?
Expedia's 325 hotels in Key West give you a great choice for your poolside getaway.
What is there to see and do in Key West?
Explore places such as Duval Street, Mallory Square and Southernmost Point while you're in Key West. The picturesque setting of Florida Keys Beaches and Audubon House and Tropical Gardens showcase the area's natural beauty. Key West appeals to visitors with its beautiful ocean views, great live music scene and bar scene.
When is the best time to book a hotel with a pool in Key West?
Taking the local weather in Key West into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Key West is 956 mm.

Explore a world of travel with Expedia