A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Hotels with Swimming Pools in Florida Keys

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Check availability on Florida Keys Hotels with Swimming Pools

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Florida Keys hotels with a pool

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A balcony with wicker furniture and a view of the ocean and palm trees.
View from room
A hotel room with a balcony, a bed, a desk, and two chairs.

1. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
S$244
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A two-story building with a balcony, a sign reading 'LAPENSIONE INN', and a flag.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.

2. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
  • Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.
S$215
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
A balcony with a view of a body of water, a pool, and outdoor seating.
A balcony with a view of the ocean, a round table, and two chairs.
An outdoor dining area with tables and chairs, overlooking a body of water.
A waterfront property with a large building, a smaller structure with a thatched roof, and several boats docked.

3. Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
  • Float away in a paradise with two outdoor pools, poolside dining, and marina views.
S$193
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn & Suites by Marriott Marathon Florida Keys
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A beach with palm trees and lounge chairs.
A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

4. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
S$274
includes taxes & fees
26 Oct - 27 Oct
Chesapeake Beach Resort
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.
A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.
A hotel room with a large bed, a desk, a chair, a balcony with a view of the ocean, and a painting on the wall.
A bathroom with a large mirror, a sink, and a shower area with a patterned tile wall.

5. The Laureate Key West

The Laureate Key West
New Town
  • Splash into relaxation with indoor and outdoor pools surrounded by plush loungers and umbrellas at this waterfront retreat.
S$265
includes taxes & fees
20 Oct - 21 Oct
The Laureate Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern bathroom with a shower, a sink, and a mirror.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

6. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
  • Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.
S$215
includes taxes & fees
27 Oct - 28 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

7. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
  • Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
S$253
includes taxes & fees
25 Oct - 26 Oct
Blue Flamingo Resort Key West
A waterfront hotel with a pool, palm trees, and a wooden dock.
A marina with numerous boats docked, a swimming pool, and palm trees.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

8. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.
S$251
includes taxes & fees
25 Oct - 26 Oct
Hilton Key West Resort & Marina
A large swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
Sports facility

9. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.
S$204
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Key West / The Keys Collection
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.
A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

10. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
  • Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
S$320
includes taxes & fees
27 Oct - 28 Oct
Hyatt Vacation Club at Windward Pointe, Key West
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Choose what matters most at hotels with a pool in Florida Keys

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Florida Keys

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.
A bar area with a thatched roof, wooden chairs, and a poolside view.
A hotel room with a balcony, a bed, a desk, and two chairs.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
S$244
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A modern office space with a reception desk, computer, and seating area.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
S$217
includes taxes & fees
25 Oct - 26 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
S$215
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.
A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.
A table with chairs in a lush indoor garden setting.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
S$353
includes taxes & fees
17 Oct - 18 Oct
Lighthouse Hotel - Key West Historic Inns
Pool
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
S$253
includes taxes & fees
25 Oct - 26 Oct
Blue Flamingo Resort Key West
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
S$251
includes taxes & fees
26 Oct - 27 Oct
Courtyard by Marriott Key West Waterfront
A swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
Sports facility

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
S$204
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Key West / The Keys Collection
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.
A marina with boats docked, a beach resort building, and palm trees.
A pool area with blue lounge chairs, a hot tub, and a covered seating area.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
S$238
includes taxes & fees
18 Oct - 19 Oct
Ibis Bay Beach Resort
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
S$215
includes taxes & fees
27 Oct - 28 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A hotel with a swimming pool, balconies, and a view of the sea.
A balcony with a view of the ocean, a table, chairs, and a railing.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
S$435
includes taxes & fees
29 Oct - 30 Oct
Hyatt Centric Key West Resort and Spa
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4-star hotels with pools in Florida Keys

A hotel with a swimming pool, balconies, and a view of the sea.
A balcony with a view of the ocean, a table, chairs, and a railing.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
S$435
includes taxes & fees
29 Oct - 30 Oct
Hyatt Centric Key West Resort and Spa
A hotel with a covered entrance, multiple balconies, and palm trees.
A waterfront hotel with multiple balconies, a dock, and boats.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
S$424
includes taxes & fees
18 Oct - 19 Oct
Opal Key Resort & Marina, Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
S$398
includes taxes & fees
25 Oct - 26 Oct
Casa Marina Key West, Curio Collection by Hilton
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
S$215
includes taxes & fees
27 Oct - 28 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and a cabana.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.
A balcony with a table set for breakfast, overlooking the sea.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
S$508
includes taxes & fees
29 Oct - 30 Oct
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A balcony with a view of the ocean, a sofa, and a massage table.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
S$475
includes taxes & fees
2 Nov - 3 Nov
Pier House Resort & Spa
A deck with sun loungers and a railing overlooking the sea.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
S$326
includes taxes & fees
25 Oct - 26 Oct
Southernmost Beach Resort and Guesthouses
A swimming pool surrounded by palm trees and a natural rock formation.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.
A covered outdoor seating area with a pool in the background.

Havana Cabana at Key West

Havana Cabana at Key West
New Town
S$291
includes taxes & fees
1 Nov - 2 Nov
Havana Cabana at Key West
A beach with a wooden pier, palm trees, and beach umbrellas.
A modern bar area with a central island, white bar stools, and a view of the ocean.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
S$307
includes taxes & fees
26 Oct - 27 Oct
The Reach Key West, Curio Collection by Hilton
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A bar area with a wooden counter, bar stools, and potted plants.

Islander Resort

Islander Resort
Matecumbe
S$394
includes taxes & fees
18 Oct - 19 Oct
Islander Resort
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

Islander Resort

Islander Resort

10/10 Excellent
"Very nice experience and cosy hotel in the Keys, super recommended!"
Clara 1-night trip
Posted 5 hours ago
Islander Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great location"
Dianne 5-night trip
Posted 8 hours ago
Chesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"What to say really. We had a n absolute nightmare of a day on our way down to the hotel. We were due to land at Key West at 1200 but that turned into landing in Miami and then an 8 hour delay before finally touching down. The staff at the hotel were great contacting us throughout the day and being so friendly and attentive! We arrived finally at the hotel at 2230 and Robin at the check in was so fantastic staying back for us to be able to be checked in! We even got an upgrade. The only downside was due to the mess caused by flights, we were in the room for just a few hours. The resort was beautiful. The view from The balcony to the sea. The room was just so unbelievable it was like the stuff you get in dreams. Such a beautiful resort, beautiful room and I am certain we will be back! Thank you!"
Peter 1-night trip
Posted 18 hours ago
Lime Tree Bay Resort
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"We love staying at Hawks Cay we have been going for years. The Property amenities are amazing. However, the Villa we stayed at (7039) was in horrible condition. Roaches in kitchen and bathroom, Shades on windows were broken in rooms. The jacuzzi outside was dirty and we were not able to use. We were extremely disappointed to have found it in that condition. I reported to the front office when we checked out. I didn't bother saying anything while there because I am pretty sure they didn't have another one available."
Ivonne 3-night trip
Posted 21 hours ago
Hawks Cay Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"The room was clean and the property was beautiful."
Darryl 2-night trip
Posted 22 hours ago
Reefhouse Resort & Marina
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."
Manuel 1-night trip
Posted 2 days ago
Waterside Suites & Marina
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

10/10 Excellent
"As soon as we"
Stephen 4-night trip
Posted 3 days ago
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

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