Hotels with a Pool in Key West

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Hotels with a Pool in Key West

A balcony with a view of a pool area, palm trees, and outdoor seating.

A large conference room with round tables, chairs, and a central carpeted area.

A modern bathroom with a shower, a sink, and a mirror.

A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.

1. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Outdoor pool
Poolside bar
Pool loungers
Near the beach

$127

$177 total

includes taxes & fees

Oct 27 - Oct 28

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.'

2. Hilton Garden Inn Key West / The Keys Collection

New Town

Outdoor pool
Poolside bar
Pool loungers
Hot tub

$119

$162 total

includes taxes & fees

Oct 29 - Oct 30

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

A two-story yellow house with a porch, white railings, and green shutters.

A hotel with a pool, bicycles, and lush greenery.

A bathroom with a shower, toilet, and sink, featuring a black and white hexagonal tile pattern on the floor and walls.

3. Silver Palms Inn & Historic Homes

Old Town Key West

Outdoor pool
Near the beach

$99

$179 total

includes taxes & fees

Oct 25 - Oct 26

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 balcony with wicker furniture and a view of the ocean and palm trees.

4. Hampton Inn Key West FL

Key West

Outdoor pool
Poolside bar
Pool loungers

$159

$179 total

includes taxes & fees

Oct 13 - Oct 14

A waterfront hotel with a pool, palm trees, and a wooden dock.

A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.

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.

5. Hilton Key West Resort & Marina

Stock Island

6 outdoor pools
Poolside bar
Pool loungers

$131

$205 total

includes taxes & fees

Oct 28 - Oct 29

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 couple holding hands in a tropical setting with palm trees and greenery.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

6. Blue Flamingo Resort Key West

New Town

2 outdoor pools
2 poolside bars
Pool loungers
Hot tub

$125

$197 total

includes taxes & fees

Oct 13 - Oct 14

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 view of the sea, and a spiral staircase.

A balcony with wicker furniture, a red chair, and a lamp.

7. Beachside Resort & Residences

Key West

Outdoor pool
Poolside bar
Pool loungers
On private beach
Hot tub

$107

$216 total

includes taxes & fees

Oct 13 - Oct 14

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.

A beach with a wooden pier, palm trees, and beach umbrellas.

8. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Outdoor pool
Poolside bar
Pool loungers
On private beach
Full-service spa

$178

$267 total

includes taxes & fees

Oct 25 - Oct 26

A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

A covered porch with wicker chairs, a view of the street, and a palm tree.

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A lush garden with a variety of tropical plants and a paved walkway.

9. Duval House

Old Town Key West

Pool loungers
Near the beach

$179

$223 total

includes taxes & fees

Oct 26 - Oct 27

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

A covered outdoor area with a pool, palm trees, and lounge chairs.

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A room with a view of the ocean, a white railing, and wicker chairs.

10. The Marker Key West Harbor Resort

Key West Historic District

3 outdoor pools
Poolside bar
Pool loungers
Near the beach

$195

$283 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a large bed, a view of a swimming pool, and a balcony with outdoor seating.

A two-story house with a balcony, surrounded by palm trees and a clear blue sky.

A bedroom with a large bed, a view of a swimming pool, and an open door leading to an outdoor seating area.

A wooden deck with wicker furniture, a white staircase, and a lush garden area.

11. Heron House - Adult Only

Old Town Key West

Outdoor pool
Near the beach

$120

$169 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

12. Havana Cabana at Key West

New Town

Outdoor pool
Poolside bar
Pool loungers
Hot tub

$159

$243 total

includes taxes & fees

Oct 13 - Oct 14

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

A grand staircase with ornate railings and a chandelier.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

A large, two-story house with a prominent tower and a covered porch.

13. Southernmost House - Adult Exclusive

Old Town Key West

Outdoor pool
Pool loungers
Near the beach

$149

$294 total

includes taxes & fees

Oct 27 - Oct 28

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 wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A spacious lobby with green sofas, a coffee table, and a dining area.

14. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

2 outdoor pools
Pool loungers
On private beach
Full-service spa

$216

$310 total

includes taxes & fees

Oct 25 - Oct 26

A wooden deck with lush greenery and a pool area.

An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

15. Douglas House - Adults Only

Old Town Key West

Outdoor pool

$155

$191 total

includes taxes & fees

Oct 13 - Oct 14

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 spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

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.

16. The Laureate Key West

New Town

Outdoor pool
Pool loungers

$159

$207 total

includes taxes & fees

Oct 25 - Oct 26

A hotel with a swimming pool, balconies, and a view of the sea.

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 marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A balcony with a table and chairs, overlooking a turquoise sea with boats and a distant shoreline.

17. Hyatt Centric Key West Resort and Spa

Key West Historic District

Outdoor pool
Poolside bar
Pool loungers
Near the beach
Full-service spa

$237

$336 total

includes taxes & fees

Oct 14 - Oct 15

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building with balconies.

A living room with a sofa, chairs, a coffee table, and a view of the outdoors through large sliding glass doors.

A covered outdoor area with a white railing, palm trees, and a view of a multi-story building.

A balcony with a table set for two, overlooking a beach and ocean.

18. Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Outdoor pool

$215

$276 total

includes taxes & fees

Oct 28 - Oct 29

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.

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.

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

New Town

Outdoor pool
Poolside bar

$143

$189 total

includes taxes & fees

Oct 25 - Oct 26

A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

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 balcony with white railings, a view of the beach, and palm trees.

A beachfront hotel with multiple-story buildings, palm trees, and a sandy beach.

20. Southernmost Beach Resort and Guesthouses

Old Town Key West

3 outdoor pools
2 poolside bars
Pool loungers
Near the beach
Full-service spa

$174

$269 total

includes taxes & fees

Oct 26 - Oct 27

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Discover your perfect hotel with a pool in Key West

Breakfast included

4 stars

Hot tub

5 stars

Spa

Hotels with pools and free breakfast in Key West

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.

Silver Palms Inn & Historic Homes

Old Town Key West

$99

$179 total

includes taxes & fees

Oct 25 - Oct 26

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$178

$267 total

includes taxes & fees

Oct 25 - Oct 26

Havana Cabana at Key West

New Town

$159

$243 total

includes taxes & fees

Oct 13 - Oct 14

A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

The Marker Key West Harbor Resort

Key West Historic District

$195

$283 total

includes taxes & fees

Oct 25 - Oct 26

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.

Southernmost Beach Resort and Guesthouses

Old Town Key West

$174

$269 total

includes taxes & fees

Oct 26 - Oct 27

A building with a white exterior, a large red awning, and a gated entrance.

A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

A pool area with lounge chairs and a lifebuoy.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

Authors of Key West Guest House

Key West Historic District

$149

$168 total

includes taxes & fees

Oct 13 - Oct 14

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A beach with palm trees, lounge chairs, and umbrellas.

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

A tall palm tree with a white building in the background.

Parrot Key Hotel & Villas

Northside Resort

$127

$200 total

includes taxes & fees

Oct 13 - Oct 14

A conference room with a patterned carpet, multiple tables, chairs, and two chandeliers.

A hotel room with a bed, a desk, a chair, a balcony with a view, and a ceiling fan.

DoubleTree Resort by Hilton Grand Key - Key West

Key West

$127

$177 total

includes taxes & fees

Oct 27 - Oct 28

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$216

$310 total

includes taxes & fees

Oct 25 - Oct 26

Heron House - Adult Only

Old Town Key West

$120

$169 total

includes taxes & fees

Oct 13 - Oct 14

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4-star hotels with pools in Key West

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$178

$267 total

includes taxes & fees

Oct 25 - Oct 26

Southernmost Beach Resort and Guesthouses

Old Town Key West

$174

$269 total

includes taxes & fees

Oct 26 - Oct 27

The Marker Key West Harbor Resort

Key West Historic District

$195

$283 total

includes taxes & fees

Oct 25 - Oct 26

DoubleTree Resort by Hilton Grand Key - Key West

Key West

$127

$177 total

includes taxes & fees

Oct 27 - Oct 28

Havana Cabana at Key West

New Town

$159

$243 total

includes taxes & fees

Oct 13 - Oct 14

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$216

$310 total

includes taxes & fees

Oct 25 - Oct 26

Parrot Key Hotel & Villas

Northside Resort

$127

$200 total

includes taxes & fees

Oct 13 - Oct 14

Southernmost House - Adult Exclusive

Old Town Key West

$149

$294 total

includes taxes & fees

Oct 27 - Oct 28

A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Key West Historic District

$237

$336 total

includes taxes & fees

Oct 14 - Oct 15

A marina with boats docked, a pool area, and a building with a white facade.

A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

Hilton Key West Resort & Marina

Stock Island

$131

$205 total

includes taxes & fees

Oct 28 - Oct 29

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Hotels with pools and hot tubs in Key West

Havana Cabana at Key West

New Town

$159

$243 total

includes taxes & fees

Oct 13 - Oct 14

A spacious lobby with a marble floor, leather sofas, and large potted plants.

A beach with palm trees, clear blue water, and a pier extending into the sea.

Beachside Resort & Residences

Key West

$107

$216 total

includes taxes & fees

Oct 13 - Oct 14

Blue Flamingo Resort Key West

New Town

$125

$197 total

includes taxes & fees

Oct 13 - Oct 14

A swimming pool with lounge chairs and palm trees.

Hilton Garden Inn Key West / The Keys Collection

New Town

$119

$162 total

includes taxes & fees

Oct 29 - Oct 30

A balcony with a view of a street, a bench, and a potted plant.

A multi-story building with a ground-level commercial space featuring a brightly lit storefront.

A hotel lobby with a bar area, seating, and a fireplace.

Pegasus International Hotel

Old Town Key West

$121

$186 total

includes taxes & fees

Oct 13 - Oct 14

A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

A cozy room with a wicker chair, a small table with a bottle and glasses, and a view of a yellow room through an open door.

A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

Tropical Inn

Old Town Key West

$175

$221 total

includes taxes & fees

Oct 13 - Oct 14

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.

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

$208

$279 total

includes taxes & fees

Oct 26 - Oct 27

A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.

A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

Eden House

Key West Historic District

$140

$177 total

includes taxes & fees

Oct 26 - Oct 27

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

A swimming pool with lounge chairs, surrounded by palm trees and greenery.

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

$278

$313 total

includes taxes & fees

Oct 27 - Oct 28

A spacious room with a wooden floor, white furniture, and large windows.

A paved pathway surrounded by lush greenery and palm trees.

A modern living room with a sofa, two armchairs, a coffee table, and a small table with a lamp. There is a large window with shutters, an air conditioning unit, and a view of greenery outside.

A white building with a covered porch, potted plants, and a white picket fence.

Paradise Inn Key West - Adults Only

Old Town Key West

$194

$269 total

includes taxes & fees

Oct 26 - Oct 27

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 neighborhoods in Key West

A large red brick building with arched windows and a prominent entrance.

A lighthouse, a white building with green shutters, and a small white structure with a wooden roof.

A white lighthouse with a black top, a white building with green shutters, and a palm tree.

A white lighthouse, a white building with green shutters, and a white picket fence.

A white lighthouse with a black top, surrounded by lush green trees and a white picket fence.

Old Town Key West

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

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A row of pastel-colored houses with white railings and a clear blue sky.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

A white church with a bell tower and a large arched entrance.

A historic street with ornate buildings, including a church with twin spires and a building with a balcony.

A person skydiving over a coastal landscape with clear turquoise waters, green vegetation, and a road.

New Town

New Town gives you a quieter slice of Key West living away from the tourist crowds. This peaceful residential area offers wide streets for strolling and a glimpse into authentic island life. Nearby Smathers Beach and the Key West Tropical Forest provide natural escapes when you need a break from the bustle. Budget-friendly chain hotels and vacation rentals make this area wallet-friendly for longer stays. Cuban-American eateries and family restaurants offer affordable meals, while shopping plazas with grocery stores help you feel right at home. A car is handy, but free parking is plentiful throughout the neighborhood.

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The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

A street with a pharmacy, a theater, and a yellow building.

A historic building with ornate architecture, a balcony, and a coat of arms.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

Downtown Key West dazzles with its historic charm and non-stop energy. Wander Duval Street's lively scene, visit Hemingway's famous six-toed cat sanctuary, or catch the sunset celebration at Mallory Square where fire-breathers and musicians perform against stunning Gulf backdrops. The neighborhood's Victorian mansions with gingerbread trim and weathered coral stone churches create a unique tropical atmosphere. The area serves up fresh seafood from casual waterfront joints to upscale restaurants. Most attractions sit within a walkable six-block radius, though you can hop on the Conch Tour Train when your feet need a break. Boutique hotels and historic inns with tropical courtyards offer charming places to crash after experiencing the legendary bar scene.

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A white lighthouse surrounded by lush greenery and a white picket fence.

A wooden sign for Ernest Hemingway Home with admission prices and operating hours.

A white lighthouse with a black top, surrounded by lush green trees and a clear blue sky.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

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A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

A vintage red bus with 'Old Town Trolley Tours' written on it, parked on a paved area with people around.

A large sculpture with text indicating it is the Southernmost Point of the Continental U.S.A. and 90 miles to Cuba.

A colorful marker labeled 'Southernmost Point' in Key West, FL, with a view of the ocean in the background.

Uptown - Upper Duval

Key West's Uptown - Upper Duval neighborhood has a host of places to visit such as Duval Street and Florida Keys Beaches.

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Top landmarks in Key West

Duval Street

9.2/10 (20,928 reviews)

If you want to give your credit card some exercise, head out to Duval Street, a popular place for shoppers in Key West Historic District. Splash some more cash at Mallory Dock and We Cycle Key West.

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Southernmost Point

8.8/10 (17,214 reviews)

If you're planning a bit of sightseeing head to Southernmost Point— just one of the monuments in Old Town Key West. Why not take a stroll along the beaches and watch the sunset while you're here?

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Mallory Square

9.2/10 (15,939 reviews)

Mallory Square is worth passing through for a few pics when in Key West Historic District. Why not take a stroll along the beaches and watch the sunset while you're here?

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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)

Whether you want to collect beach glass or watch the sunset, Smathers Beach is a spot you might want to check out, located 1.7 mi (2.8 km) from central Key West. If you want to continue walking by the waves, head to Clarence S. Higgs Memorial Beach Park located nearby.

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Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)

Ernest Hemingway Home and Museum is just one of the attractions in Old Town Key West, Key West so you might want to stop by during your trip. Why not take a stroll along the beaches and watch the sunset while you're here? If you want to experience more of the culture Key West has to offer, head to Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Key West Butterfly and Nature Conservatory.

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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)

Fort Zachary Taylor Historic State Park is 0.6 mi (1 km) from central Key West, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?

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South Beach

8.4/10 (5,461 reviews)

If being by the water is a major draw, South Beach is a spot you might want to check out, located 0.7 mi (1.1 km) from central Key West. Catch the sunset by the shore at Simonton Beach, just a short walk away.

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