Top 10 Hotels with Pool & Accommodation in Florida Keys from AU$110

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

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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.

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

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

1. Havana Cabana at Key West

New Town

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

AU$247

includes taxes & fees

22 Sept - 23 Sept

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

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

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

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

2. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Oceanfront relaxation awaits with heated pool sanctuary and spa pool retreat, mere steps from Key West's beautiful Smathers Beach.

AU$333

includes taxes & fees

22 Sept - 23 Sept

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.

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

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

Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.

AU$219

includes taxes & fees

8 Sept - 9 Sept

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

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 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.

4. Chesapeake Beach Resort

Matecumbe

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

AU$259

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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.

AU$218

includes taxes & fees

15 Sept - 16 Sept

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

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.

A hotel room with a balcony overlooking a marina and the ocean.

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.

AU$261

includes taxes & fees

27 Sept - 28 Sept

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.

AU$216

includes taxes & fees

22 Sept - 23 Sept

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.

AU$238

includes taxes & fees

13 Sept - 14 Sept

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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

Havana Cabana at Key West

New Town

AU$247

includes taxes & fees

22 Sept - 23 Sept

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

AU$219

includes taxes & fees

8 Sept - 9 Sept

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

Chesapeake Beach Resort

Matecumbe

AU$259

includes taxes & fees

7 Sept - 8 Sept

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

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

Authors of Key West Guest House

Key West Historic District

AU$116

includes taxes & fees

28 Sept - 29 Sept

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

A pink building with a white door, a balcony with a white railing, and a view of a pool area.

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

AU$207

includes taxes & fees

28 Sept - 29 Sept

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

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.

Hampton Inn Key West FL

Key West

AU$216

includes taxes & fees

22 Sept - 23 Sept

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

A waterfront property with a white facade, palm trees, and a street view.

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

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

Duval Inn

Old Town Key West

AU$240

includes taxes & fees

1 Oct - 2 Oct

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

Hilton Key West Resort & Marina

Stock Island

AU$261

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

Parrot Key Hotel & Villas

Northside Resort

AU$286

includes taxes & fees

15 Sept - 16 Sept

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

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.

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

Ibis Bay Beach Resort

Northside Resort

AU$203

includes taxes & fees

7 Sept - 8 Sept

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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 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.

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.

Hyatt Centric Key West Resort and Spa

Key West Historic District

AU$408

includes taxes & fees

28 Sept - 29 Sept

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 pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

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

AU$504

includes taxes & fees

21 Sept - 22 Sept

A pool area with lounge chairs and a cabana.

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

A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

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

Key West Historic District

AU$452

includes taxes & fees

30 Sept - 1 Oct

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

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