Hotels with Swimming Pool in Key West, Florida

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Check availability on Key West Hotels with Swimming Pool

Top Key West Hotels with Swimming 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, (1129)
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.
The price is P5,149
P7,454 total
includes taxes & fees
Dec 2 - Dec 3
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, (1709)
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.
The price is P7,036
P11,230 total
includes taxes & fees
Dec 4 - Dec 5
Blue Flamingo Resort 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, (1698)
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.
The price is P6,531
P10,330 total
includes taxes & fees
Nov 30 - Dec 1
Beachside Resort & Residences
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas
The Laureate Key West

The Laureate Key West

3.5 star property
New Town
  • Outdoor pool
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1008)
Cooling cloths and refreshing towels await poolside after exploring nearby beaches or water activities. The clean, well-maintained swimming areas complement spacious rooms with stunning ocean views from private balconies.
The price is P9,370
P12,199 total
includes taxes & fees
Nov 23 - Nov 24
The Laureate Key West
Outdoor pool
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 star property
Key West
  • Outdoor pool
  • Near the beach
  • Hot tub
9.6 out of 10, Exceptional, (1012)
Poolside paradise beckons at this oceanfront hotel, featuring a heated outdoor pool, relaxing hot tub, and convenient tiki restaurant. Spacious rooms offer balconies with stunning sunrise and sunset views, creating a peaceful seaside escape.
The price is P15,008
P19,542 total
includes taxes & fees
Dec 8 - Dec 9
Hyatt Vacation Club at Windward Pointe, Key West
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, (1010)
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.
The price is P7,512
P10,444 total
includes taxes & fees
Dec 2 - Dec 3
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool
Fairfield Inn & Suites by Marriott Key West at the Keys Collection

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

3.5 star property
New Town
  • Outdoor pool
  • Poolside bar
8.6 out of 10, Excellent, (1001)
Surrounded by lush courtyards, the sparkling outdoor pool creates a peaceful retreat for sun-soaked relaxation. Guests appreciate the convenient poolside bar, bicycle rentals for island exploration, and proximity to water activities like snorkeling and kayaking.
The price is P6,305
P8,748 total
includes taxes & fees
Dec 1 - Dec 2
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
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, (1194)
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.
The price is P7,602
P11,203 total
includes taxes & fees
Nov 26 - Nov 27
The Southernmost Inn - Adults Only
Exterior
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
Stock Island
  • 6 outdoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (1743)
Sparkling pools invite sunbathers to lounge in free cabanas while sipping drinks from the poolside bar. Beyond the water's edge, this luxury resort offers kayaking, fishing excursions, and complimentary bicycles for island exploration.
The price is P9,606
P14,362 total
includes taxes & fees
Nov 30 - Dec 1
Oceans Edge Key West Resort, Hotel & Marina
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, (1164)
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.
The price is P7,602
P11,933 total
includes taxes & fees
Dec 3 - Dec 4
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.
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Top Key West Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Amenities"
Brian Dennis 3-night trip
Posted 4 days ago
Casa Marina Key West, Curio Collection by Hilton

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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 276 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. The Perry Hotel & Marina Key West: Hotel located near Smathers Beach. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. 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 276 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.