Find Hotels with a Pool in Key West, FL

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Key West Hotels with a Pool

Tonight
Nov 7 - Nov 8
Tomorrow
Nov 8 - Nov 9
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top Key West Hotels with a Pool

Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
New Town
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
8.0 out of 10, Very Good, (1113)
Swimmers splash into vacation mode at the outdoor pool oasis, complete with stylish cabanas, comfortable loungers, and a refreshing poolside bar. Beyond the water, this Key West hotel offers bicycle rentals, fitness facilities, and convenient shuttle service.
$112 nightly
The price is $126
Dec 1 - Dec 2
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property
New Town
  • 2 outdoor pools
  • 2 poolside bars
  • Pool loungers
  • Hot tub
8.0 out of 10, Very Good, (1663)
Cooling waters beckon at 2 outdoor pools complete with private cabanas, sun loungers, and poolside bars serving refreshing drinks. Active guests enjoy mini golf, bicycling, and a 24-hour fitness center between dips.
$157 nightly
The price is $177
Nov 17 - Nov 18
Total with taxes and fees
Blue Flamingo Resort Key West
Outdoor pool, open 7:00 AM to 10:00 PM, free cabanas, sun loungers
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3.0 star property
New Town
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Near the beach
7.8 out of 10, Good, (1169)
Sparkling waters beckon at the inviting outdoor pool, complete with complimentary cabanas and sun loungers available from 7:00 AM to 10:00 PM. Guests savor refreshing cocktails from the poolside tiki bar while enjoying American cuisine in a tropical paradise setting.
$126 nightly
The price is $142
Nov 30 - Dec 1
Total with taxes and fees
Fairfield Inn and Suites by Marriott Key West
Outdoor pool
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4.0 star property
Key West
  • Outdoor pool
  • Direct access to the beach
8.8 out of 10, Excellent, (1768)
Immerse in the inviting outdoor pool, complemented by white sand beach access just steps away. Guests appreciate the tropical landscaped grounds, convenient shuttle service, and delicious restaurant offerings at this peaceful island retreat.
$235 nightly
The price is $264
Dec 2 - Dec 3
Total with taxes and fees
Margaritaville Beach House Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4.0 star property
Stock Island
  • 2 outdoor pools
  • 2 poolside bars
  • Pool loungers
9.4 out of 10, Exceptional, (1142)
Immerse in 2 outdoor pools with elegant loungers and refreshing drinks from poolside bars. Beyond the aquatic sanctuary, guests enjoy bicycling, boating excursions, and dining at waterfront restaurants with breathtaking sunset views.
$187 nightly
The price is $210
Nov 12 - Nov 13
Total with taxes and fees
The Perry Hotel & Marina Key West
Outdoor pool, pool umbrellas, sun loungers
Beachside Resort & Residences

Beachside Resort & Residences

3.5 star property
Key West
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
  • Hot tub
8.6 out of 10, Excellent, (1666)
Sparkling waters beckon at the outdoor pool, where sun loungers, umbrellas, and poolside cocktail service create an idyllic retreat. Marina activities, water sports, and a complimentary shuttle to downtown enhance this beachfront sanctuary.
$187 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Beachside Resort & Residences
4 outdoor pools, pool umbrellas, sun loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4.0 star property
Northside Resort
  • 4 outdoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (1150)
Aquatic luxury defines this island escape where 4 pristine pools invite endless relaxation. Comfortable loungers, pool umbrellas, and a vibrant poolside bar create perfect days, while nearby water adventures from kayaking to sailing await the adventurous.
$194 nightly
The price is $218
Nov 18 - Nov 19
Total with taxes and fees
Parrot Key Hotel & Villas
Building design
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3.0 star property
Old Town Key West
  • 2 outdoor pools
  • Pool loungers
  • Near the beach
  • Hot tub
8.2 out of 10, Very Good, (1174)
Poolside serenity awaits at this Victorian adults-only haven with 2 sparkling outdoor pools and a soothing hot tub. Complimentary breakfast, bike rentals, and proximity to Duval Street create a perfect balance of relaxation and exploration.
$149 nightly
The price is $167
Nov 10 - Nov 11
Total with taxes and fees
The Southernmost Inn - Adults Only
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
Key West
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Near the beach
8.0 out of 10, Very Good, (1001)
Splash into vacation mode at the sun-drenched outdoor pool, complete with complimentary cabanas and a lively poolside bar. Beyond aquatic pleasures, this resort offers bicycles for island exploration, a shuttle to nearby beaches, and an American restaurant with al fresco dining.
$169 nightly
The price is $190
Nov 18 - Nov 19
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 star property
Key West
  • Outdoor pool
  • Hot tub
9.4 out of 10, Exceptional, (1043)
Aquatic pleasures await at this eco-certified Keys haven where swimmers enjoy a sparkling outdoor pool after snorkeling adventures. A steaming hot tub soothes muscles while barbecue grills and concierge services enhance vacation days.
$307 nightly
The price is $345
Nov 19 - Nov 20
Total with taxes and fees
Hyatt Vacation Club at Beach House, 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.
View all properties

Top Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Wonderful place to stay. Uber pickup was easy. Trolly available across the street for trolly. We had great dining options."
Teresa Weatherford 4-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses

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 272 places to stay with pools. While you're here, you can explore attractions like Duval Street, and then relax and unwind poolside at one of the accommodations in Key West that travelers like for their pools.
What are some hotels with pools in Key West?
Parrot Key Hotel & Villas: Hotel located near Duval Street. Features a beach shuttle, 4 outdoor pools, and complimentary wireless internet access. Blue Flamingo Resort Key West: Hotel located near Smathers Beach. Offers 2 restaurants, 2 outdoor pools, and 2 pool bars. DoubleTree Resort by Hilton Grand Key - Key West: Resort located near Smathers Beach. Provides complimentary wired internet access, a pool, and a beach shuttle. Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. Hilton Garden Inn Key West / The Keys Collection: Hotel located near Smathers Beach. Offers 2 restaurants, a pool, and complimentary wired internet access.
How many hotels with pools are there in Key West?
Expedia's 272 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 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.

Explore a world of travel with Expedia