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

Hotels with Pool & Resorts in Florida Keys from NZ$140

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Florida Keys Hotels with Pool

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 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 hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.

1. 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.
NZ$300
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 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.

2. 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.
NZ$340
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
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 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.

3. 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.
NZ$368
includes taxes & fees
18 Oct - 19 Oct
The Laureate 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 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.

4. 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.
NZ$351
includes taxes & fees
26 Oct - 27 Oct
Blue Flamingo Resort Key West
A large swimming pool with lounge chairs and palm trees.
A modern living room with a sectional sofa, a small round table, and a potted plant.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
Sports facility

5. 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 spa pool for ultimate relaxation.
NZ$262
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Key West / The Keys Collection
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 balcony with a view of the ocean, a round table, and two chairs.
A bar area with a long counter, bar stools, and a view of the water.

6. 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.
NZ$268
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

7. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
NZ$382
includes taxes & fees
20 Oct - 21 Oct
Chesapeake Beach Resort
A swimming pool surrounded by palm trees and a natural rock formation.
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.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

8. Havana Cabana at Key West

Havana Cabana at Key West
New Town
  • Poolside paradise awaits with spa pool, dining, and bar service at this vibrant Key West oasis.
NZ$403
includes taxes & fees
1 Nov - 2 Nov
Havana Cabana at 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 pathway leading to a white gazebo with a view of a lighthouse in the distance.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.

9. 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.
NZ$490
includes taxes & fees
17 Oct - 18 Oct
Lighthouse Hotel - Key West Historic Inns
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A beach view with a wooden pier, palm trees, and a sunset over the water.
A balcony with wicker furniture, a red chair, and a lamp.
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

10. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
NZ$404
includes taxes & fees
29 Oct - 30 Oct
Beachside Resort & Residences
View all properties

Choose what matters most at hotels with a pool in Florida Keys

Breakfast included
4 stars
5 stars
Spa pool
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
NZ$340
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
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.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
NZ$318
includes taxes & fees
26 Oct - 27 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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 swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
NZ$300
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 bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
NZ$490
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 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
NZ$351
includes taxes & fees
26 Oct - 27 Oct
Blue Flamingo Resort Key West
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A modern restaurant with a wooden counter, seating area, and large windows.
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.

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
NZ$348
includes taxes & fees
26 Oct - 27 Oct
Courtyard by Marriott Key West Waterfront
A swimming pool with lounge chairs and palm trees.
A modern living room with a sectional sofa, a small round table, and a potted plant.
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
NZ$262
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 pool area with blue lounge chairs, a hot tub, and a covered seating area.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
NZ$330
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
NZ$299
includes taxes & fees
28 Oct - 29 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 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
NZ$603
includes taxes & fees
29 Oct - 30 Oct
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
NZ$603
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 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
NZ$589
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 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
NZ$552
includes taxes & fees
1 Nov - 2 Nov
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
NZ$299
includes taxes & fees
28 Oct - 29 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and a cabana.
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 waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
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
NZ$704
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 resort with a beach, a dock, and a water view.
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.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
NZ$659
includes taxes & fees
2 Nov - 3 Nov
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
NZ$451
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 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.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

Havana Cabana at Key West

Havana Cabana at Key West
New Town
NZ$403
includes taxes & fees
1 Nov - 2 Nov
Havana Cabana at Key West
A beach with a wooden pier, palm trees, and beach umbrellas.
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.
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
NZ$425
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 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
NZ$546
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.
View all properties

Top Florida Keys Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great location"
Dianne 5-night trip
Posted 6 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 16 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 16 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 20 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

Explore a world of travel with Expedia