A sailboat on calm water during sunset.

Dredgers Key Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Dredgers Key holiday rentals

1. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is HK$2,111
HK$4,025 total
includes taxes & fees
27 Sept - 28 Sept
Two Bedroom Residence With Balcony
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is HK$770
HK$2,207 total
includes taxes & fees
27 Sept - 28 Sept
Aqua Lodges at Hurricane Hole Marina
A white house with a porch, a sign reading "The Bayview House," and a small garden with a tree and a planter.

3. The Caroline Suite | 1 bedroom condo w/shared pool

The Caroline Suite | 1 bedroom condo w/shared pool
Key West Historic District
9.0 out of 10, Wonderful, (36 reviews)
"Great place!! Highly recommend and would love staying there again. "
United States
Jeff A.
The price is HK$1,989
HK$3,644 total
includes taxes & fees
2 Oct - 3 Oct
The Caroline Suite | 1 bedroom condo w/shared pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

4. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is HK$1,363
HK$3,700 total
includes taxes & fees
27 Sept - 28 Sept
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A wide sandy beach with palm trees and a clear sky.

5. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (48 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is HK$1,961
HK$3,033 total
includes taxes & fees
27 Sept - 28 Sept
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A swimming pool with a wooden deck, a covered patio area, and a building with large windows and a covered porch.

6. BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (134 reviews)
"Great location to everything in Key West. Exactly as advertised."
United States
Jennifer B.
The price is HK$4,313
HK$10,265 total
includes taxes & fees
2 Oct - 3 Oct
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

7. The Butterfly Nest | Newly Updated w/ Shared Pool

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (48 reviews)
"Had a great time place is lovely "
United States
Sarah P.
The price is HK$1,363
HK$3,699 total
includes taxes & fees
2 Oct - 3 Oct
The Butterfly Nest | Newly Updated w/ Shared Pool

8. Waterfront Dock Pool Pet Friendly Near Duval St

Waterfront Dock Pool Pet Friendly Near Duval St
Meadows
9.8 out of 10, Exceptional, (33 reviews)
"Great location and property for our group. Host was super easy to work with. Thank you for a wonderful stay!"
United States
Melissa M.
Waterfront Dock Pool Pet Friendly Near Duval St
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

9. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is HK$1,659
HK$3,843 total
includes taxes & fees
28 Sept - 29 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wide sandy beach with palm trees and a clear sky.

10. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is HK$1,961
HK$3,033 total
includes taxes & fees
28 Sept - 29 Sept
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

11. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is HK$1,424
HK$2,331 total
includes taxes & fees
27 Sept - 28 Sept
Island View 1BR Residence With Balcony

12. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
The price is HK$3,080
HK$5,404 total
includes taxes & fees
26 Oct - 27 Oct
Waterfront Condo Dock Pool Near Duval St
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

13. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is HK$1,306
HK$2,288 total
includes taxes & fees
27 Sept - 28 Sept
Poolside Cottage #411
A hot tub with a view of a marina and boats during sunset.

14. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is HK$2,510
HK$2,988 total
includes taxes & fees
2 Oct - 3 Oct
Living the Dream Key West Style
A beach with a sailboat, palm trees, and beach chairs.

15. Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Key West
9.0 out of 10, Wonderful, (144 reviews)
"Easy check in. Accommodations were very good as advertised. "
United States
Anonymous traveller
The price is HK$3,883
HK$4,619 total
includes taxes & fees
28 Sept - 29 Sept
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
A coastal scene with a wooden pier, rocky breakwaters, and a clear view of the sea.

16. Galleon Resort Efficiency in the old town

Galleon Resort Efficiency in the old town
Key West Historic District
9.6 out of 10, Exceptional, (174 reviews)
"Everything was great! We love this place."
United States
Sheena S.
The price is HK$2,314
HK$2,768 total
includes taxes & fees
11 Oct - 12 Oct
Galleon Resort Efficiency in the old town
A modern living room with a glass dining table, grey chairs, and a white sofa.

17. Rooftop Penthouse

Rooftop Penthouse
Old Town Key West
10.0 out of 10, Exceptional, (55 reviews)
"This was a great stay! Great location house was clean and had several things for us to use! "
United States
Abigail Y.
The price is HK$5,170
HK$8,725 total
includes taxes & fees
2 Oct - 3 Oct
Rooftop Penthouse
A beach with a sailboat, palm trees, and beach chairs.

18. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"We loved the location."
United States
Aneesah D.
The price is HK$5,094
HK$6,060 total
includes taxes & fees
2 Oct - 3 Oct
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
A beach with a sailboat, palm trees, and beach chairs.

19. Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (218 reviews)
"The two bedroom apartment offered everything we needed, and the pool and hot tub were welcome additions. We liked that it was close to the airport."
United States
Ann A.
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
A two-story building with balconies, surrounded by lush greenery and palm trees.

20. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (35 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
The price is HK$3,530
HK$5,593 total
includes taxes & fees
3 Oct - 4 Oct
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dredgers Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"Basic and pretty clean, rooms need updating overall. Shuttle is nice"
Kandi 3-night trip
Posted 1 hour ago
DoubleTree Resort by Hilton Grand Key - Key West

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