Find Hotels with a Pool in Florida Keys

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Check availability on Florida Keys Hotels with a Pool

Top Florida Keys Hotels with a Pool

Lime Tree Bay Resort

3.5 star property
Long Key
  • 3 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1095)
Refreshing pools surrounded by comfortable loungers create an aquatic paradise at this beachfront resort. Kayaking, tennis, and yoga complement the water experience, while Florida Boy restaurant serves delicious meals after sun-drenched adventures.
Lime Tree Bay Resort

Chesapeake Beach Resort

3.5 star property
Matecumbe
  • 2 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1568)
Pool enthusiasts savor 2 pristine outdoor pools surrounded by comfortable loungers, perfect for sunbathing between kayaking excursions. Family-friendly with adult supervision required, this refreshing oasis complements fishing and boating adventures.
The price is ¥21,680
¥33,093 total
includes taxes & fees
Nov 17 - Nov 18
Chesapeake Beach Resort

Captain Pips Marina & Hideaway

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (1002)
Swimming enthusiasts rejoice at the sun-drenched pool surrounded by comfortable loungers, perfect for relaxation after kayaking, snorkeling, or fishing excursions. This hotel combines maritime charm with convenient amenities including free bicycle rentals and a seafood restaurant.
The price is ¥10,478
¥16,136 total
includes taxes & fees
Nov 23 - Nov 24
Captain Pips Marina & Hideaway

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
New Town
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
7.8 out of 10, Good, (1120)
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 ¥13,484
¥19,519 total
includes taxes & fees
Dec 1 - Dec 2
Hilton Garden Inn Key West / The Keys Collection

Banana Bay Resort & Marina

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
  • Near the beach
  • Hot tub
7.6 out of 10, Good, (1010)
Splash into relaxation at the hotel's peaceful outdoor pool, a refreshing retreat after exploring the marina or nearby Sombrero Beach. Free bicycle rentals, outdoor tennis courts, and pickleball provide active options for adventurous travelers.
The price is ¥17,962
¥26,298 total
includes taxes & fees
Nov 27 - Nov 28
Banana Bay Resort & Marina

Amara Cay Resort

4.0 star property
Matecumbe
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
8.8 out of 10, Excellent, (1249)
Aquatic adventures await beyond the sun-drenched pool deck with its attentive bar service. From kayaking and snorkeling to fishing off the pier, this resort combines relaxation with exploration, all complemented by beachfront dining and stunning ocean views.
The price is ¥21,752
¥34,735 total
includes taxes & fees
Dec 1 - Dec 2
Amara Cay Resort

Havana Cabana at Key West

4.0 star property
New Town
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (1746)
Floating in the massive lagoon-style pool, guests discover tropical relaxation with refreshing cocktails from the poolside bar. Beyond swimming, this hotel offers bike rentals, concierge services, and delicious Cuban cuisine at the poolside restaurant.
The price is ¥19,477
¥32,025 total
includes taxes & fees
Dec 15 - Dec 16
Havana Cabana at 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, (1686)
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 ¥13,897
¥24,332 total
includes taxes & fees
Nov 16 - Nov 17
Blue Flamingo Resort 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, (1773)
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 ¥27,693
¥40,864 total
includes taxes & fees
Dec 2 - Dec 3
Margaritaville Beach House Key West

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

4.0 star property
Marathon
  • 4 outdoor pools
  • Poolside bar
  • Pool loungers
  • Direct access to the beach
  • Full-service spa
8.8 out of 10, Excellent, (1274)
Poolside paradise awaits with sun loungers, umbrellas, and refreshing cocktail service amid stunning harbor views. Beyond aquatic relaxation, guests enjoy complimentary bicycles, Caribbean dining, and proximity to Sombrero Beach.
The price is ¥21,429
¥29,927 total
includes taxes & fees
Nov 20 - Nov 21
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
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 Florida Keys Hotel Reviews

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