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Check availability on Dredgers Key Hotels with a Pool

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Our top choices for Dredgers Key hotels with a pool

A large swimming pool with lounge chairs and palm trees.

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

1. 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 $150

CA $209 total

includes taxes & fees

Oct 8 - Oct 9

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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

2. 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 $183

CA $246 total

includes taxes & fees

Oct 4 - Oct 5

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.

3. Beachside Resort & Residences

Key West

Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.

CA $124

CA $276 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

4. 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 $269 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 cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

5. Havana Cabana at Key West

New Town

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

CA $179

CA $292 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A covered deck with white railings and blue Adirondack chairs overlooking a river with palm trees.

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

6. Parrot Key Hotel & Villas

Northside Resort

Splash into paradise at four tropical pools with poolside dining and coastal shuttles.

CA $183

CA $287 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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.

7. 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 $170

CA $239 total

includes taxes & fees

Oct 8 - Oct 9

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

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

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.

8. The Laureate Key West

New Town

Splash into relaxation with indoor and outdoor pools surrounded by plush loungers and umbrellas at this waterfront retreat.

CA $226

CA $294 total

includes taxes & fees

Oct 4 - Oct 5

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Choose what matters most at hotels with a pool in Dredgers Key

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Dredgers Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Great shuttle service"

Beachside Resort & Residences

10/10 Excellent

"Good"

Blue Flamingo Resort Key West

8/10 Good

"Bar service was good. No Hot tub at main pool. Did have one on property next door. Easy access but a little bit of a drive to Deval street."

Southwinds Motel

10/10 Excellent

"Clean room, nice pool, nice staff. Good little Cuban restaurant and grocery store across the street. Loved it."

Parrot Key Hotel & Villas

8/10 Good

"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"

Pier House Resort & Spa

10/10 Excellent

"Pier house is the best place in Key West! Won’t stay anywhere else. Staff is incredible. Looking forward to this year."

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"The property was immaculate, the staff friendly and the location was perfect. We love that the resort allows you access to The Reach, which is basically next door. You are able to use all of their amenities as well and charge them to Your room. We had a beach front room with a balcony. It was beautiful!"

The Perry Hotel & Marina Key West

10/10 Excellent

"Hotel was great. All of the staff were friendly and accommodating"

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"

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Check availability on Dredgers Key Hotels with a Pool

Our top choices for Dredgers Key hotels with a pool

1. Hilton Garden Inn Key West / The Keys Collection