Book the Best Hotels with POOL in Florida Keys in 2026

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

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Check availability on Florida Keys Hotels with a Pool

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Our top choices for Florida Keys hotels with a pool

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.

An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

1. Havana Cabana at Key West

New Town

Poolside paradise awaits with hot tub, dining, and bar service at this vibrant Key West oasis.

CA $141

CA $246 total

includes taxes & fees

Sep 22 - Sep 23

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean 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.

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

2. 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 $237

CA $329 total

includes taxes & fees

Sep 22 - Sep 23

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

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

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

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

3. 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 $110

CA $217 total

includes taxes & fees

Sep 8 - Sep 9

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 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.

4. Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

CA $154

CA $251 total

includes taxes & fees

Oct 5 - Oct 6

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

A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

An outdoor patio with tables and chairs, umbrellas, and palm trees.

5. 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 $152

CA $217 total

includes taxes & fees

Sep 15 - Sep 16

A poolside area with lounge chairs and a view of boats in the background.

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 breakfast setting with a table, chairs, a vase with flowers, and a city view.

6. 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 $157

CA $259 total

includes taxes & fees

Sep 20 - Sep 21

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.

7. Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

CA $191

CA $215 total

includes taxes & fees

Sep 20 - Sep 21

A resort with a swimming pool, lounge chairs, 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

Long Key

A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.

CA $155

CA $236 total

includes taxes & fees

Sep 7 - Sep 8

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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

Havana Cabana at Key West

New Town

CA $141

CA $246 total

includes taxes & fees

Sep 22 - Sep 23

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

Silver Palms Inn & Historic Homes

Old Town Key West

CA $110

CA $217 total

includes taxes & fees

Sep 8 - Sep 9

A beach with palm trees and lounge chairs.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

Chesapeake Beach Resort

Matecumbe

CA $154

CA $251 total

includes taxes & fees

Oct 5 - Oct 6

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

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

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.

Authors of Key West Guest House

Key West Historic District

CA $102

CA $115 total

includes taxes & fees

Oct 1 - Oct 2

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.

A hotel with a white facade, multiple balconies, and lush tropical landscaping.

The Palms Hotel

Old Town Key West

CA $156

CA $206 total

includes taxes & fees

Sep 28 - Sep 29

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

Key West

CA $191

CA $215 total

includes taxes & fees

Sep 20 - Sep 21

A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

A garden with a statue of two figures, lush greenery, and a building in the background.

A poolside area with lounge chairs and umbrellas, a bar, and a staircase leading to a house.

A bedroom with a large bed, wooden headboard, two bedside lamps, and a floral wall art piece.

Duval Inn

Old Town Key West

CA $150

CA $238 total

includes taxes & fees

Oct 1 - Oct 2

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

Hilton Key West Resort & Marina

Stock Island

CA $157

CA $259 total

includes taxes & fees

Sep 20 - Sep 21

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

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.

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

Parrot Key Hotel & Villas

Northside Resort

CA $182

CA $284 total

includes taxes & fees

Sep 14 - Sep 15

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 beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

Ibis Bay Beach Resort

Northside Resort

CA $138

CA $200 total

includes taxes & fees

Sep 7 - Sep 8

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

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

Hyatt Centric Key West Resort and Spa

Key West Historic District

CA $274

CA $405 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

Pier House Resort & Spa

Key West Historic District

CA $360

CA $501 total

includes taxes & fees

Sep 16 - Sep 17

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 balcony with a table set for breakfast, overlooking the sea.

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

Ocean Key Resort - A Noble House Resort

Key West Historic District

CA $304

CA $449 total

includes taxes & fees

Sep 28 - Sep 29

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 waterfront hotel with multiple balconies, a dock, and boats.

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