Florida Keys Hotels with Swimming Pool

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Check availability on Florida Keys Hotels with Swimming Pools

Top Florida Keys Hotels with Swimming Pools

Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 star property
Long Key
  • 3 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1092)
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
Outdoor spa tub
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property
Matecumbe
  • 2 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1565)
Pool enthusiasts savour 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 RM591
RM900 total
includes taxes & fees
12 Nov - 13 Nov
Chesapeake Beach Resort
Exterior
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (1012)
Swimming enthusiasts rejoice at the sun-drenched pool surrounded by comfortable loungers, perfect for relaxation after kayaking, snorkelling, or fishing excursions. This hotel combines maritime charm with convenient amenities including free bicycle rentals and a seafood restaurant.
The price is RM321
RM479 total
includes taxes & fees
16 Nov - 17 Nov
Captain Pips Marina & Hideaway
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 RM364
RM527 total
includes taxes & fees
1 Dec - 2 Dec
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, pool umbrellas, pool loungers
Banana Bay Resort & Marina

Banana Bay Resort & Marina

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
  • Near the beach
  • Hot tub
7.6 out of 10, Good, (1004)
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 travellers.
The price is RM447
RM667 total
includes taxes & fees
11 Nov - 12 Nov
Banana Bay Resort & Marina
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 hot tub, and convenient tiki restaurant. Spacious rooms offer balconies with stunning sunrise and sunset views, creating a peaceful seaside escape.
The price is RM1,125
RM1,454 total
includes taxes & fees
1 Dec - 2 Dec
Hyatt Vacation Club at Windward Pointe, Key West
3 bars/lounges, poolside bar
Amara Cay Resort

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 snorkelling to fishing off the pier, this resort combines relaxation with exploration, all complemented by beachfront dining and stunning ocean views.
The price is RM645
RM1,003 total
includes taxes & fees
30 Nov - 1 Dec
Amara Cay Resort
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 RM747
RM1,103 total
includes taxes & fees
2 Dec - 3 Dec
Margaritaville Beach House Key West
Outdoor pool, pool umbrellas, pool loungers
Waterside Suites & Marina

Waterside Suites & Marina

3.5 star property
Key Largo
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1117)
Floating in the pristine outdoor pool while watching boats navigate the canal creates a perfect holiday rhythm. Comfortable sun loungers under shady umbrellas provide all-day relaxation, with water activities like parasailing and kayaking just steps away.
The price is RM512
RM693 total
includes taxes & fees
11 Nov - 12 Nov
Waterside Suites & Marina
Outdoor pool, open 8:00 AM to 11:00 PM, pool loungers
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

3.5 star property
Tavernier
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
8.4 out of 10, Very good, (1006)
Sparkling waters beckon from the outdoor pool, surrounded by comfortable loungers for soaking up the Florida sun. After swimming, guests savour oceanfront dining at the Island Grill Restaurant or sip refreshing drinks at the poolside bar.
The price is RM567
RM713 total
includes taxes & fees
17 Nov - 18 Nov
Ocean Pointe Suites at Key Largo
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 Florida Keys Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
" Well staffed and very prompt in requests. Our first visit there recommended by my children that have stayed often. Very efficient and polite and courteous in this ugly world it was a welcome feeling. We will be back"
Deborah 3-night trip
Posted 22 hours ago
Cheeca Lodge & Spa

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