Book the Best Hotels with POOL in Lower Florida Keys in 2026

A coastal landscape with clear turquoise waters, a long bridge, and a small island with buildings.

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Check availability on Lower Florida Keys Hotels with a Pool

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Our top choices for Lower Florida Keys hotels with a pool

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

A waterfront building with a flat roof, large windows, and a balcony.

1. Sugar Loaf Lodge

Summerland Key

Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.

CA $141

CA $159 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool surrounded by palm trees and a natural rock formation.

A covered outdoor seating area with a pool in the background.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

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

2. Havana Cabana at Key West

New Town

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

CA $182

CA $295 total

includes taxes & fees

Nov 2 - Nov 3

A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.

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.

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

3. 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 $168

CA $270 total

includes taxes & fees

Oct 4 - Oct 5

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.'

4. 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 $158

CA $218 total

includes taxes & fees

Oct 8 - Oct 9

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.

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

A hotel with a central courtyard, palm trees, and a fountain.

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 $175

CA $245 total

includes taxes & fees

Oct 11 - Oct 12

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.

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 $180

CA $286 total

includes taxes & fees

Oct 12 - Oct 13

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.

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 $241

CA $271 total

includes taxes & fees

Oct 25 - Oct 26

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 wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

A modern office space with a reception desk, computer, and seating area.

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

New Town

Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.

CA $184

CA $247 total

includes taxes & fees

Oct 4 - Oct 5

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

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Lower Florida Keys

An outdoor patio area with tables and chairs, a bar, and a pool.

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.

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

New Town

CA $184

CA $247 total

includes taxes & fees

Oct 4 - Oct 5

A bar area with a thatched roof, wooden chairs, and a poolside view.

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

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 $241

CA $271 total

includes taxes & fees

Oct 25 - Oct 26

DoubleTree Resort by Hilton Grand Key - Key West

Key West

CA $175

CA $245 total

includes taxes & fees

Oct 11 - Oct 12

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

CA $180

CA $286 total

includes taxes & fees

Oct 12 - Oct 13

A swimming pool with lounge chairs and palm trees.

Hilton Garden Inn Key West / The Keys Collection

New Town

CA $158

CA $218 total

includes taxes & fees

Oct 8 - Oct 9

Blue Flamingo Resort Key West

New Town

CA $168

CA $270 total

includes taxes & fees

Oct 4 - Oct 5

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

Northside Resort

CA $275

CA $309 total

includes taxes & fees

Oct 26 - Oct 27

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

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

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

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

Parrot Key Hotel & Villas

Northside Resort

CA $180

CA $284 total

includes taxes & fees

Oct 11 - Oct 12

Havana Cabana at Key West

New Town

CA $182

CA $295 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

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

A marina with boats docked, a beach resort building, and palm trees.

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

Ibis Bay Beach Resort

Northside Resort

CA $181

CA $250 total

includes taxes & fees

Oct 4 - Oct 5

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4-star hotels with pools in Lower Florida Keys

DoubleTree Resort by Hilton Grand Key - Key West

Key West

CA $175

CA $245 total

includes taxes & fees

Oct 11 - Oct 12

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

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with boats docked, a swimming pool, and palm trees.

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.