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

Our top choices for Florida Keys hotels with a pool

A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

1. Rock Reef Resort

Rock Reef Resort
Rock Harbor
  • Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
$87 nightly
$98 total
Oct 21 - Oct 22
Total with taxes and fees
Rock Reef Resort
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
$175 nightly
$197 total
Oct 26 - Oct 27
Total with taxes and fees
Chesapeake Beach Resort
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.
A waterfront property with a large building, a smaller structure with a thatched roof, and several boats docked.
An outdoor dining area with tables and chairs, overlooking a body of water.

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.
$134 nightly
$151 total
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Marathon Florida Keys
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 yellow house with a porch, white railings, and green shutters.
A two-story building with a balcony, a sign reading 'LAPENSIONE INN', and a flag.

4. 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.
$159 nightly
$179 total
Oct 25 - Oct 26
Total with taxes and fees
Silver Palms Inn & Historic Homes
A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
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.

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.
$175 nightly
$197 total
Oct 25 - Oct 26
Total with taxes and fees
Blue Flamingo Resort Key West
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.
A bathroom with a large mirror, a sink, and a shower area with a patterned tile wall.
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 spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

6. 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.
$184 nightly
$207 total
Oct 18 - Oct 19
Total with taxes and fees
The Laureate Key West
A pool area with lounge chairs, a thatched-roof structure, and a view of the ocean.
A modern living room with a large sectional sofa, a flat-screen TV, and a view of the sea through large windows.
A bar area with wicker chairs and a thatched roof, overlooking a body of water with boats.
A modern kitchen with a central island, various appliances, and hanging pendant lights.

7. Hampton Inn Marathon - Florida Keys

Hampton Inn Marathon - Florida Keys
Marathon
  • Sip cocktails while floating away worries at this Florida Keys escape with a poolside bar and hot tub sanctuary.
$130 nightly
$147 total
Oct 26 - Oct 27
Total with taxes and fees
Hampton Inn Marathon - Florida Keys
A resort with a swimming pool, lounge chairs, and palm trees.
A balcony with wicker furniture and a view of the ocean and palm trees.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.
A spacious living area with a large island, wooden furniture, and a ceiling fan.

8. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
  • A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
$131 nightly
$148 total
Nov 1 - Nov 2
Total with taxes and fees
Lime Tree Bay Resort
A waterfront hotel with a pool, palm trees, and a wooden dock.
A clear view of turquoise ocean water and a blue sky with clouds.
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.

9. 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.
$174 nightly
$196 total
Oct 27 - Oct 28
Total with taxes and fees
Hilton Key West Resort & Marina
A swimming pool with a hot tub, palm trees, and a building with a staircase.
A beach with lounge chairs and umbrellas, palm trees, and a building with balconies.
A hotel corridor with a view of the beach, palm trees, and outdoor seating.
A wooden deck with two chairs and a table, overlooking a beach with palm trees and the ocean.

10. Rainbow Bend Resort

Rainbow Bend Resort
Marathon
  • Float away in the turquoise pool with ocean views before retreating to the poolside hot tub at sunset.
$142 nightly
$160 total
Oct 18 - Oct 19
Total with taxes and fees
Rainbow Bend Resort
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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 balcony, a bed, a desk, and two chairs.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
$169 nightly
$190 total
Oct 25 - Oct 26
Total with taxes and fees
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
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.
A modern office space with a reception desk, computer, and seating area.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
$150 nightly
$169 total
Oct 25 - Oct 26
Total with taxes and fees
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 yellow house with a porch, white railings, and green shutters.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
$159 nightly
$179 total
Oct 25 - Oct 26
Total with taxes and fees
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 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.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
$245 nightly
$276 total
Oct 17 - Oct 18
Total with taxes and fees
Lighthouse Hotel - Key West Historic Inns
Pool
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
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.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
$175 nightly
$197 total
Oct 25 - Oct 26
Total with taxes and fees
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 modern restaurant with a wooden counter, seating area, and large windows.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
$174 nightly
$196 total
Oct 26 - Oct 27
Total with taxes and fees
Courtyard by Marriott Key West Waterfront
A swimming pool with lounge chairs and palm trees.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
Sports facility
A modern living room with a sectional sofa, a small round table, and a potted plant.

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
$131 nightly
$147 total
Oct 28 - Oct 29
Total with taxes and fees
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 hotel with multiple colorful buildings, a pool area, and a boat dock.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
$202 nightly
$228 total
Oct 18 - Oct 19
Total with taxes and fees
Ibis Bay Beach Resort
A balcony with a view of a pool area, palm trees, and outdoor seating.
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.
A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
$149 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - 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 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.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
$316 nightly
$356 total
Oct 19 - Oct 20
Total with taxes and fees
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 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 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.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
$316 nightly
$356 total
Oct 19 - Oct 20
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
A hotel with a covered entrance, multiple balconies, and palm trees.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.
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
$294 nightly
$331 total
Oct 18 - Oct 19
Total with taxes and fees
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
$276 nightly
$310 total
Oct 25 - Oct 26
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
A balcony with a view of a pool area, palm trees, and outdoor seating.
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.
A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
$149 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and a cabana.
A balcony with a table set for breakfast, overlooking the sea.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
$371 nightly
$417 total
Oct 20 - Oct 21
Total with taxes and fees
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A resort with a beach, a dock, and a water view.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A balcony with a view of the ocean, a sofa, and a massage table.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
$350 nightly
$394 total
Nov 2 - Nov 3
Total with taxes and fees
Pier House Resort & Spa
A deck with sun loungers and a railing overlooking the sea.
A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, 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 beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
$225 nightly
$253 total
Oct 25 - Oct 26
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
A swimming pool surrounded by palm trees and a natural rock formation.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
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
$201 nightly
$227 total
Nov 1 - Nov 2
Total with taxes and fees
Havana Cabana at Key West
A beach with a wooden pier, palm trees, and beach umbrellas.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables and chairs, overlooking the ocean.
A modern bar area with a central island, white bar stools, 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
$152 nightly
$171 total
Oct 28 - Oct 29
Total with taxes and fees
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 paved pathway leading to a beach with palm trees and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Islander Resort
Matecumbe
$293 nightly
$329 total
Nov 2 - Nov 3
Total with taxes and fees
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great location"
Dianne 5-night trip
Posted 5 hours ago
Chesapeake Beach Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

8/10 Good
"The lady at the desk TJ was kind and helpful. Very nice room and area"
Anna 1-night trip
Posted 15 hours ago
Bayside Inn Key Largo
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 15 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 19 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 19 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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