Find Hotels with a Pool in Key West, FL

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Key West Hotels with a Pool

Our top choices for Key West hotels with a pool

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Old Town Key West
10.0 out of 10, Exceptional, (1,008 reviews)
"Small pool and hot tub were more than adequate."
United States
James
The price is AED 979
AED 1,101 total
includes taxes & fees
25 May - 26 May
Almond Tree Inn Hotel - Adults Only

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (948 reviews)
"Beautiful courtyards and pools."
United States
Casey
The price is AED 628
AED 706 total
includes taxes & fees
13 May - 14 May
Simonton Court Historic Inn & Cottages

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (1,002 reviews)
"Staff members were very nice, pool area"
United States
Pamela
The price is AED 999
AED 1,124 total
includes taxes & fees
25 May - 26 May
Orchid Key Inn - Adults Only

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (1,004 reviews)
"The pool area was beautiful and the pools themselves were perfect."
United States
SUSAN
The price is AED 1,135
AED 1,483 total
includes taxes & fees
26 May - 27 May
The Marquesa Hotel

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (603 reviews)
"H20 was a fantastic stay and surprisingly to us both the pool on the roof and our very own plunge pool were heated and we made use of them both."
United Kingdom
Simon
The price is AED 1,329
AED 1,743 total
includes taxes & fees
2 Jun - 3 Jun
H2O Suites - Adults Only

The Gardens Hotel

The Gardens Hotel
4.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (1,003 reviews)
"Lovely pool and gardens, very friendly staff."
United States
Jill
The price is AED 1,030
AED 1,158 total
includes taxes & fees
11 May - 12 May
The Gardens Hotel

Key West Villas

Key West Villas
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (261 reviews)
"Pool was quaint but refreshing."
United States
Jessica
The price is AED 955
AED 1,075 total
includes taxes & fees
4 Jun - 5 Jun
Key West Villas

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (143 reviews)
"The morning breakfast and afternoon happy hour at the pool were both great for meeting the other guests and making everything relaxed and social."
United States
Jacob
The price is AED 658
AED 887 total
includes taxes & fees
12 May - 13 May
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Island City House Hotel

Island City House Hotel
3.0 star property
Key West Historic District
9.6 out of 10, Exceptional, (1,002 reviews)
"Centrally located, very clean, well kept grounds, nice pool."
United States
charles
The price is AED 854
AED 961 total
includes taxes & fees
4 Jun - 5 Jun
Island City House Hotel

Santa Maria Suites

Santa Maria Suites
4.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,004 reviews)
"Wonderful pool"
United States
lloyd
The price is AED 1,245
AED 1,649 total
includes taxes & fees
1 Jun - 2 Jun
Santa Maria Suites
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.

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

Hotels with pools and free breakfast in Key West

Hotels with pools and hot tubs in Key West

4-star hotels with pools in Key West

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.

Top Key West Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Key West?
If taking it easy by the pool is your idea of a great getaway, you might want to think about Key West, which has 328 places to stay with pools. While you're here, you can explore attractions like Duval Street and Florida Keys Beaches, and then relax and unwind poolside at one of the accommodations 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 pools, and 2 pool bars. Ibis Bay Beach Resort: Hotel located near Florida Keys Beaches. Offers a private beach, an outdoor pool, and daily. DoubleTree Resort by Hilton Grand Key - Key West: Resort located near Florida Keys Beaches. Provides complimentary wired internet access, a pool, and a beach shuttle. Parrot Key Hotel & Villas: Hotel located near Florida Keys Beaches. Features a beach shuttle, 4 outdoor pools, and complimentary wireless internet access. Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Offers 2 pool bars, 3 outdoor pools, and a full-service spa.
How many hotels with pools are there in Key West?
Expedia's 328 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 like Duval Street and Florida Keys Beaches while you're in Key West. The picturesque setting of Audubon House and Tropical Gardens and Key West Butterfly and Nature Conservatory 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 into account the local weather in Key West is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Key West is 38 inches.