A sailboat on calm water during sunset.

Dredgers Key Hotel Guide - Hotels with Pool in Dredgers Key, Key West

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Check availability on Dredgers Key Hotels with Pool

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

Our top choices for Dredgers Key hotels with a pool

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A balcony with wicker furniture, a view of the sea, and a spiral staircase.
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.

1. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
€171
includes taxes & fees
4 Oct - 5 Oct
Beachside Resort & Residences
A large swimming pool with lounge chairs and palm trees.
Sports facility
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.'

2. 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.
€130
includes taxes & fees
7 Oct - 8 Oct
Hilton Garden Inn Key West / The Keys Collection
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 covered deck with white railings and blue Adirondack chairs overlooking a river with palm trees.
A beach with palm trees, lounge chairs, and umbrellas.

3. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
  • Splash into paradise at four tropical pools with poolside dining and coastal shuttles.
€182
includes taxes & fees
12 Oct - 13 Oct
Parrot Key Hotel & Villas
A pool area with lounge chairs and a lifebuoy.
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.

4. Authors of Key West Guest House

Authors of Key West Guest House
Key West Historic District
  • Soak up the sun at a literary retreat with poolside bliss, where tranquility awaits in a convenient Key West location.
€81
includes taxes & fees
4 Oct - 5 Oct
Authors of Key West Guest House
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 covered outdoor seating area with a pool in the background.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.

5. 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.
€181
includes taxes & fees
1 Nov - 2 Nov
Havana Cabana at Key West
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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

6. 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.
€167
includes taxes & fees
7 Oct - 8 Oct
Blue Flamingo Resort Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
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.

7. 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.
€140
includes taxes & fees
7 Oct - 8 Oct
DoubleTree Resort by Hilton Grand Key - Key West
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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

8. 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.
€153
includes taxes & fees
4 Oct - 5 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.
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.
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.

9. The Laureate Key West

The Laureate Key West
New Town
  • Splash into relaxation with indoor and outdoor pools surrounded by plush loungers and umbrellas at this waterfront retreat.
€183
includes taxes & fees
12 Oct - 13 Oct
The Laureate Key West
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.
A two-story building with a white picket fence, a mailbox, and a small tree in front.
A lush garden with a variety of tropical plants and a paved walkway.
A covered porch with wicker chairs, a view of the street, and a palm tree.

10. Duval House

Duval House
Old Town Key West
  • Soothing heated pool in the heart of Key West creates an inviting oasis amid tropical gardens at this bed and breakfast.
€126
includes taxes & fees
5 Oct - 6 Oct
Duval House
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

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 less than an hour 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 2 hours ago
Parrot Key Hotel & Villas
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

10/10 Excellent
"It is a great option away from all the action."
Micheal 4-night trip
Posted 4 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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 6 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 7 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 9 hours ago
The Perry Hotel & Marina Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Had a great time!"
Nathan 4-night trip
Posted 22 hours ago
Winslow's Bungalows - Key West Historic Inns
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The room was clean. No daily housekeeping. The staff were pleasant and quiet helpful. Breakfast was outstanding. It was alacart and you have to pay per item. Over all this was the most relaxing vacation I've been on. Loved it!"
Harry 1-night trip
Posted 1 day ago
Beachside Resort & Residences
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

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