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

Find Hotels with a Pool in Florida Keys

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Check availability on Florida Keys Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Florida Keys hotels with a pool

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.
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.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
  • Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.
￥18,376
￥25,125 total
includes taxes & fees
Oct 29 - Oct 30
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.
A hotel with a pool, bicycles, and lush greenery.
A two-story building with a balcony, a sign reading 'LAPENSIONE INN', and a flag.
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.
￥14,123
￥26,589 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
A white outdoor seating area with a pool view, featuring white chairs and a small table with a vase of flowers.
A waterfront hotel with multiple balconies, a dock, and boats.
A large resort building with multiple balconies, palm trees, and a well-lit entrance area.
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

3. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
￥40,995
￥52,353 total
includes taxes & fees
Oct 26 - Oct 27
Opal Key Resort & Marina, Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
Breakfast area
View from room
A balcony with wicker furniture and a view of the ocean and palm trees.

4. 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.
￥26,749
￥30,093 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
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 spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A couple holding hands in a tropical setting with palm trees and greenery.

5. 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.
￥18,376
￥29,575 total
includes taxes & fees
Oct 29 - Oct 30
Blue Flamingo Resort Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

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.
￥16,968
￥24,432 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
A poolside area with wicker furniture, a covered seating area, and a white building with a balcony.
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.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.

7. Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
  • Take a dip in Key West's serene outdoor pool oasis, where relaxation meets historic charm just steps from Duval Street.
￥31,656
￥43,626 total
includes taxes & fees
Oct 26 - Oct 27
Lighthouse Hotel - Key West Historic Inns
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
A multi-story hotel with balconies, palm trees, and a pool area.
A marina with boats docked, a swimming pool, and palm trees.

8. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
  • Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.
￥15,173
￥26,328 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina Key West
A swimming pool with lounge chairs, surrounded by palm trees and greenery.
A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
A hotel named 'Almond Tree Inn' with a covered parking area, surrounded by lush greenery and palm trees.
A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

9. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Old Town Key West
￥37,924
￥42,664 total
includes taxes & fees
Oct 25 - Oct 26
Almond Tree Inn Hotel - Adults Only
A pool area with lounge chairs, a pool, and a white picket fence.
A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.
A white decorative sculpture in a garden area with a white fence and a building in the background.
An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".

10. Southwinds Motel

Southwinds Motel
Old Town Key West
  • Dive into refreshing fun at this Key West hotel with two sparkling pools and tropical charm all around.
￥22,033
￥30,137 total
includes taxes & fees
Oct 26 - Oct 27
Southwinds Motel
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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 hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A bar area with a thatched roof, wooden chairs, and a poolside view.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
￥26,749
￥30,093 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
Pool
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A couple holding hands in a tropical setting with palm trees and greenery.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
￥18,376
￥29,575 total
includes taxes & fees
Oct 29 - Oct 30
Blue Flamingo Resort Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.
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
￥18,376
￥25,125 total
includes taxes & fees
Oct 29 - Oct 30
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A hotel with a swimming pool, balconies, and a view of the sea.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A balcony with a view of the ocean, a table, chairs, and a railing.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
￥37,091
￥52,783 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
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.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
￥25,038
￥38,866 total
includes taxes & fees
Oct 28 - Oct 29
The Reach Key West, Curio Collection by Hilton
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
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
￥14,123
￥26,589 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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
￥28,016
￥41,627 total
includes taxes & fees
Nov 19 - Nov 20
Havana Cabana at Key West
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.
A balcony with a view of a pool area, palm trees, and outdoor seating.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
￥16,968
￥24,432 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
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 pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A resort with a beach, a dock, and a water view.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
￥28,813
￥43,470 total
includes taxes & fees
Oct 25 - Oct 26
Pier House Resort & Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A tropical setting with palm trees and a building with a white facade and dark roof.
A covered outdoor area with a pool, palm trees, and lounge chairs.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
￥29,847
￥43,564 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
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4-star hotels with pools in Florida Keys

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 covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
￥40,995
￥52,353 total
includes taxes & fees
Oct 26 - Oct 27
Opal Key Resort & Marina, Key West
A hotel with a swimming pool, balconies, and a view of the sea.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A balcony with a view of the ocean, a table, chairs, and a railing.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
￥37,091
￥52,783 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
A deck with sun loungers and a railing overlooking 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.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
￥27,588
￥42,612 total
includes taxes & fees
Oct 26 - Oct 27
Southernmost Beach Resort and Guesthouses
A pool area with lounge chairs and a cabana.
A balcony with a table set for breakfast, overlooking the sea.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
￥47,326
￥66,063 total
includes taxes & fees
Oct 28 - Oct 29
Ocean Key Resort - A Noble House Resort
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.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
￥25,038
￥38,866 total
includes taxes & fees
Oct 28 - Oct 29
The Reach Key West, Curio Collection by Hilton
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 pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A resort with a beach, a dock, and a water view.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
￥28,813
￥43,470 total
includes taxes & fees
Oct 25 - Oct 26
Pier House Resort & Spa
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.
A balcony with a view of a pool area, palm trees, and outdoor seating.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
￥16,968
￥24,432 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
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
￥28,016
￥41,627 total
includes taxes & fees
Nov 19 - Nov 20
Havana Cabana at Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A spacious lobby with green sofas, a coffee table, and a dining area.

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
￥35,518
￥50,642 total
includes taxes & fees
Oct 28 - Oct 29
Casa Marina Key West, Curio Collection by Hilton
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A tropical setting with palm trees and a building with a white facade and dark roof.
A covered outdoor area with a pool, palm trees, and lounge chairs.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
￥29,847
￥43,564 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor 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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"The room was very nice, but had a cockroach problem. Was very disappointed about that Had one in the bed on the last night and figured it would be a pain in the middle of the night to change rooms TV In the bedroom was broken, let staff know and nothing was done about it Tried watching football game, and TV in living room area had bad reception and kept going out Otherwise the property is beautiful and wanting to go back, but would like a room with no bugs"
Matthew 2-night trip
Posted 2 hours ago
Cheeca Lodge & Spa
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"The place is very relaxing. Very clean. No bugs. Helpful polite staff. No complains at all. Just keep the fact that additional charges at check out are quite high."
Frederick 5-night trip
Posted 8 hours ago
Hawks Cay Resort
Kingsail Resort

Kingsail Resort

8/10 Good
"service to the room was not up to the standards of the rest of the resort"
Deanna 4-night trip
Posted 9 hours ago
Kingsail Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

8/10 Good
"The hotel needs more amenities and activities."
Jorge 4-night trip
Posted 11 hours ago
Reefhouse Resort & Marina
Islander Resort

Islander Resort

10/10 Excellent
"Resort was always clean during our stay. All of the staff were incredibly nice and helpful! Lots of activities on the property to keep you entertained."
Samuel 6-night trip
Posted 12 hours ago
Islander Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

8/10 Good
"I rented a suite (# 401), supposed to be the best. The problem is that I found a lot of deficiencies inside. First fan and light bulb in the room wasn’t working, no light bulb in the lamp corner of the room. Fan and light bulb not working either in dining table. The sofa was broken on the left side. My wife had to clean the stove and top of the refrigerator because too much dust and grease. I called maintenance and case was resolved more or less, but believe me for the price you paid for the suite I deserve better. Housekeeping should monitor better and check everything before rent any property. Outside the property was well maintained. Thanks to give me the the opportunity to explain a review of the place. However all staff on premises were very nice, helpful, courteous and friendly. Hope my review will be considered for future reference."
Raimundo 3-night trip
Posted 13 hours ago
Bayside Inn Key Largo
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"We always stay at Lime Tree Bay. If you find yourself driving down U.S. 1, be sure to stop and enjoy the Exceptional Service, Beauty, and one of the Best stays we have loved many times, in Layton, Lime Tree Bay and the Keys await you!"
Gabriel 1-night trip
Posted 1 day ago
Lime Tree Bay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The room we had was exceptional, the view was awesome. The bar area was a nice amenity. Although this is a pet friendly hotel, seems like some people do not feel the need to pick up after their pets, if you know what I mean. So that was why I couldn’t give the grounds a five star."
Christine 2-night trip
Posted 1 day ago
Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return ."
Tim 3-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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