Hotels with Pool & Resorts in Key West from NZ$225

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Check availability on Key West Hotels with Pool

Best Key West Hotels with Pool

Outdoor pool, open 6:00 AM to 10:00 PM, pool 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, (1116)
Swimmers splash into holiday 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 NZ$225
includes taxes & fees
1 Dec - 2 Dec
Hilton Garden Inn Key West / The Keys Collection
2 outdoor pools, open 7:00 AM to 11:00 PM, pool 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, (1676)
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 centre between dips.
The price is NZ$302
includes taxes & fees
17 Nov - 18 Nov
Blue Flamingo Resort Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, pool 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, (1144)
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.
The price is NZ$347
includes taxes & fees
26 Nov - 27 Nov
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 10:00 PM, free pool cabanas, pool 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, (1160)
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 savour refreshing cocktails from the poolside tiki bar while enjoying American cuisine in a tropical paradise setting.
The price is NZ$252
includes taxes & fees
30 Nov - 1 Dec
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, (1772)
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.
The price is NZ$470
includes taxes & fees
2 Dec - 3 Dec
Margaritaville Beach House Key West
Outdoor pool, pool umbrellas, pool 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, (1673)
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 city centre enhance this beachfront sanctuary.
The price is NZ$356
includes taxes & fees
17 Nov - 18 Nov
Beachside Resort & Residences
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, (1001)
Poolside paradise beckons at this oceanfront hotel, featuring a heated outdoor pool, relaxing spa pool, and convenient tiki restaurant. Spacious rooms offer balconies with stunning sunrise and sunset views, creating a peaceful seaside escape.
The price is NZ$619
includes taxes & fees
1 Dec - 2 Dec
Hyatt Vacation Club at Windward Pointe, Key West
4 outdoor pools, pool umbrellas, pool 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, (1156)
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 NZ$407
includes taxes & fees
18 Nov - 19 Nov
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, (1176)
Poolside serenity awaits at this Victorian adults-only haven with 2 sparkling outdoor pools and a soothing spa pool. Complimentary breakfast, bike rentals, and proximity to Duval Street create a perfect balance of relaxation and exploration.
The price is NZ$311
includes taxes & fees
12 Nov - 13 Nov
The Southernmost Inn - Adults Only
Outdoor pool, open 7:00 AM to 11:00 PM, pool 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, (1006)
Splash into holiday 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 NZ$331
includes taxes & fees
19 Nov - 20 Nov
DoubleTree Resort by Hilton Grand Key - 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.
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Top Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Excellent amenities, good location. Friendly staff. Very good bar staff and pool side kitchen fare. "
Erin 4-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses

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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 272 places to stay with pools. During your trip, you can explore attractions such as Duval Street, and then take it easy poolside at one of the accommodation options in Key West that travellers 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 swimming pools and complimentary wireless Internet access. Blue Flamingo Resort Key West: Hotel located near Smathers Beach. Offers 2 restaurants, 2 outdoor swimming pools and 2 pool bars. DoubleTree Resort by Hilton Grand Key - Key West: Resort located near Smathers Beach. Provides complimentary high-speed (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 swimming 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 high-speed (wired) Internet access.
How many hotels with pools will I find 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 such as 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 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.