A sailboat on calm water during sunset.

Find Hotels with a Pool in Dredgers Key, FL

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Check availability on Dredgers Key Hotels with a Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Dredgers Key hotels with a pool

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

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

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.
₩175,395
₩235,552 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool surrounded by palm trees and a natural rock formation.
A covered outdoor seating area with a pool in the background.
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.

2. Havana Cabana at Key West

Havana Cabana at Key West
New Town
  • Poolside paradise awaits with hot tub, dining, and bar service at this vibrant Key West oasis.
₩171,316
₩278,783 total
includes taxes & fees
Nov 1 - Nov 2
Havana Cabana at Key West
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 covered deck with white railings and blue Adirondack chairs overlooking a river with palm trees.

3. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
  • Splash into paradise at four tropical pools with poolside dining and coastal shuttles.
₩179,190
₩279,482 total
includes taxes & fees
Oct 11 - Oct 12
Parrot Key Hotel & Villas
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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.

4. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
  • Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
₩160,389
₩256,797 total
includes taxes & fees
Oct 4 - Oct 5
Blue Flamingo Resort Key West
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 water, and a railing.
A balcony with wicker furniture, a red chair, and a lamp.

5. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
₩118,685
₩263,537 total
includes taxes & fees
Oct 4 - Oct 5
Beachside Resort & Residences
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 hotel with a central courtyard, palm trees, and a fountain.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

6. DoubleTree Resort by Hilton Grand Key - Key West

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.
₩161,814
₩227,857 total
includes taxes & fees
Oct 8 - Oct 9
DoubleTree Resort by Hilton Grand Key - Key West
A white outdoor seating area with a pool view, featuring white chairs and a small table with a vase of flowers.
A deck with sun loungers, a bar area, and a view of the ocean.
A waterfront hotel with multiple balconies, a dock, and boats.
A large resort building with multiple balconies, palm trees, and a well-lit entrance area.

7. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
₩351,593
₩449,007 total
includes taxes & fees
Oct 4 - Oct 5
Opal Key Resort & Marina, Key West
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 modern living room with a sectional sofa, a small round table, and a potted plant.
Sports facility

8. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.
₩143,800
₩199,962 total
includes taxes & fees
Oct 8 - Oct 9
Hilton Garden Inn Key West / The Keys Collection
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.
Breakfast area
A balcony with wicker furniture and a view of the ocean and palm trees.

9. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
₩224,802
₩252,902 total
includes taxes & fees
Oct 7 - Oct 8
Hampton Inn Key West FL
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.
A modern restaurant with a wooden counter, seating area, and large windows.
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

10. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
  • Savor the sun in this poolside paradise with tropical gardens and a relaxing hot tub.
₩262,038
₩294,793 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
View all properties

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

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Great shuttle service"
Eric 1-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Good"
sai krishna 3-night trip
Posted 8 hours ago
Beachside Resort & Residences
Blue Flamingo Resort Key West

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."
Gary 2-night trip
Posted 9 hours ago
Blue Flamingo Resort Key West
Southwinds Motel

Southwinds Motel

10/10 Excellent
"Clean room, nice pool, nice staff. Good little Cuban restaurant and grocery store across the street. Loved it."
Ann 4-night trip
Posted 10 hours ago
Southwinds Motel
Parrot Key Hotel & Villas

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 …"
Alexandre 1-night trip
Posted 12 hours ago
Parrot Key Hotel & Villas
Pier House Resort & Spa

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."
James 5-night trip
Posted 16 hours ago
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

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!"
Amber Dawn 4-night trip
Posted 17 hours ago
Casa Marina Key West, Curio Collection by Hilton
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Hotel was great. All of the staff were friendly and accommodating"
Kellie 1-night trip
Posted 19 hours ago
The Perry Hotel & Marina Key West
Hyatt Centric Key West Resort and Spa

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!"
Christy 2-night trip
Posted 3 days ago
Hyatt Centric Key West Resort and Spa