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

Find Hotels with a Pool in Florida Keys from CA $121

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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 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.
View from room
Breakfast area

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.
CA $224
CA $252 total
includes taxes & fees
Oct 21 - Oct 22
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 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.

2. 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.
CA $164
CA $264 total
includes taxes & fees
Oct 25 - Oct 26
Blue Flamingo Resort Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A bathroom with a shower, toilet, and sink, featuring a black and white hexagonal tile pattern on the floor and walls.
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.

3. 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.
CA $126
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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 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.

4. 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.
CA $224
CA $292 total
includes taxes & fees
Oct 25 - Oct 26
The Laureate Key West
A balcony with a view of a body of water, a pool, and outdoor seating.
A waterfront property with a large building, a smaller structure with a thatched roof, and several boats docked.
A bar area with a long counter, bar stools, and a view of the water.
A balcony with a view of the ocean, a round table, and two chairs.

5. 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.
CA $189
CA $213 total
includes taxes & fees
Oct 27 - Oct 28
Fairfield Inn & Suites by Marriott Marathon Florida Keys
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

6. 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.
CA $149
CA $207 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Garden Inn Key West / The Keys Collection
A balcony with a view of a pool area, palm trees, and outdoor seating.
A modern hotel room with a balcony, a grey sofa, a red chair, a white coffee table, and a painting of a tropical scene.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

7. 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.
CA $151
CA $218 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
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.

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.
CA $167
CA $270 total
includes taxes & fees
Oct 27 - Oct 28
Hilton Key West Resort & Marina
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A beach with palm trees and lounge chairs.

9. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
CA $205
CA $310 total
includes taxes & fees
Oct 26 - Oct 27
Chesapeake Beach Resort
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean 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.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

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.
CA $251
CA $346 total
includes taxes & fees
Oct 28 - Oct 29
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 hotel room with a balcony, a bed, a desk, and two chairs.
A bar area with a thatched roof, wooden chairs, and a poolside view.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
CA $224
CA $252 total
includes taxes & fees
Oct 21 - Oct 22
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.
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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
CA $164
CA $224 total
includes taxes & fees
Oct 27 - Oct 28
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 exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.
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
CA $126
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
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 table with chairs in a lush indoor garden setting.
A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
CA $282
CA $389 total
includes taxes & fees
Oct 25 - Oct 26
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
CA $164
CA $264 total
includes taxes & fees
Oct 25 - Oct 26
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 hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.
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
CA $224
CA $252 total
includes taxes & fees
Oct 27 - Oct 28
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
CA $149
CA $207 total
includes taxes & fees
Oct 28 - Oct 29
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 pool area with blue lounge chairs, a hot tub, and a covered seating area.
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.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
CA $151
CA $216 total
includes taxes & fees
Oct 21 - Oct 22
Ibis Bay Beach Resort
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A conference room with a large white screen, multiple tables, and chairs.
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
CA $151
CA $218 total
includes taxes & fees
Oct 29 - Oct 30
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 beach wedding setup with white chairs, a wooden arch, and lanterns.
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
CA $330
CA $475 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
View all properties

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 beach wedding setup with white chairs, a wooden arch, and lanterns.
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
CA $330
CA $475 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
A hotel with a covered entrance, multiple balconies, and palm trees.
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.
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
CA $365
CA $467 total
includes taxes & fees
Oct 25 - Oct 26
Opal Key Resort & Marina, Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
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
CA $316
CA $451 total
includes taxes & fees
Oct 28 - Oct 29
Casa Marina Key West, Curio Collection by Hilton
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A conference room with a large white screen, multiple tables, and chairs.
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
CA $151
CA $218 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and a cabana.
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.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
CA $422
CA $589 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
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.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
CA $256
CA $387 total
includes taxes & fees
Oct 26 - Oct 27
Pier House Resort & 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 beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.
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
CA $246
CA $380 total
includes taxes & fees
Oct 25 - Oct 26
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
CA $241
CA $361 total
includes taxes & fees
Oct 21 - Oct 22
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.
An outdoor dining area with tables and chairs, overlooking the ocean.
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
CA $223
CA $346 total
includes taxes & fees
Oct 28 - Oct 29
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 paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

Islander Resort

Islander Resort
Matecumbe
CA $242
CA $376 total
includes taxes & fees
Nov 15 - Nov 16
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.
View all properties

Top Florida Keys Hotel Reviews

Reefhouse Resort & Marina

Reefhouse Resort & Marina

8/10 Good
"The hotel needs more amenities and activities."
Jorge 4-night trip
Posted 5 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 6 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 7 hours ago
Bayside Inn Key Largo
Kingsail Resort

Kingsail Resort

10/10 Excellent
"Buena ubicación, buen trato del personal, súper limpio. La unidad tiene cocina que es súper práctica. Lo único que no nos gustó fue que al estar hospedados en plata Baja escuchábamos todos los movimientos de los vecinos del piso superior"
Cristian 2-night trip
Posted 18 hours ago
Kingsail Resort
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 19 hours 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
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"Our villa was right next to the workers building. Not an ideal spot for a “premium” villa. Also when they were cutting lawn and blowing leaves they were blowing everything all over our rental cars. Parking was tough because I think employees were also parking in guest spots. Again I think this was due to the location of our villa. We were never told what to do with our garbage or if housekeeping would come clean. Found out later you need to specifically request it 24 hrs in advance. It was off season so nice and quite not too many people so they definitely could have put us elsewhere. Other than that we really enjoyed ourselves and plan to go back next time we would just be specific on check in about the location they put us in."
Tamara 7-night trip
Posted 2 days ago
Hawks Cay Resort

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