A sailboat on calm water during sunset.

Dredgers Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Dredgers Key holiday rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is HK$840
HK$2,289 total
includes taxes & fees
14 Oct - 15 Oct
Aqua Lodges at Hurricane Hole Marina
A wooden signpost with city names and distances in miles.

2. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (458 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is HK$770
HK$1,873 total
includes taxes & fees
19 Oct - 20 Oct
Steps from Duval, Pool on Site & Bikes Included!
Exterior

3. 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)
The price is HK$1,601
HK$2,494 total
includes taxes & fees
14 Oct - 15 Oct
Island View 1BR Residence With Balcony
A swimming pool surrounded by lush greenery, with lounge chairs and a covered seating area.

4. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (121 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
The price is HK$934
HK$2,368 total
includes taxes & fees
14 Oct - 15 Oct
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

5. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is HK$1,307
HK$2,360 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

6. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (21 reviews)
"Great facility and loved the location! "
United States
Matt R.
The price is HK$1,373
HK$3,901 total
includes taxes & fees
27 Oct - 28 Oct
The Grand Cayman | Beautifully Remodeled Key West!
A pool area with a wooden deck, a two-story building with balconies, and palm trees.

7. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (57 reviews)
"The room was functional. We loved the location and ease of getting everywhere. The pool was really nice. The only complaint is that the entire bathroom floods when you take a shower. We ended up using our flip flops to squeegee the water to the drain, because the drain is higher than the rest of the floor. Highly recommend providing a squeegee to help with flooding."
United States
Shawn
The price is HK$855
HK$2,709 total
includes taxes & fees
20 Oct - 21 Oct
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

8. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is HK$1,307
HK$2,375 total
includes taxes & fees
20 Oct - 21 Oct
Poolside Cottage #411
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

9. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is HK$1,373
HK$3,901 total
includes taxes & fees
27 Oct - 28 Oct
The Cat Island Suite | Charmingly Renovated w/ Pool
A hotel room with two beds, a ceiling fan, a TV, and a window with blinds.

10. Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (49 reviews)
"Great location"
United States
Glen V.
The price is HK$941
HK$3,268 total
includes taxes & fees
21 Oct - 22 Oct
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

11. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.8 out of 10, Exceptional, (13 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
The price is HK$1,240
HK$2,640 total
includes taxes & fees
27 Oct - 28 Oct
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

12. 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$1,373
HK$3,901 total
includes taxes & fees
27 Oct - 28 Oct
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Room

13. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is HK$1,601
HK$2,494 total
includes taxes & fees
14 Oct - 15 Oct
Resort View 1BR Suite
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

14. VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (57 reviews)
"Great crew here. From the airport shuttle to constant communication to make sure we were happy. Would highly recommend for a great getaway! Very convenient to lots of places to have fun."
United States
Jesse M.
The price is HK$855
HK$2,709 total
includes taxes & fees
25 Oct - 26 Oct
VanGogh Studio | Updated, Old Town, Heated Pool
A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

15. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (79 reviews)
"Fantastic location"
United States
Jennifer
The price is HK$1,200
HK$3,939 total
includes taxes & fees
15 Oct - 16 Oct
Duval Delight | Recently Remodeled Condo on Duval!
A multi-level wooden house with a blue staircase and white railings.

16. Underwater Cabana at Custom House Inn | On Duval!

Underwater Cabana at Custom House Inn | On Duval!
Key West Historic District
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location, spacious room. Our second time staying at this venue."
United States
Colleen L.
The price is HK$1,200
HK$3,539 total
includes taxes & fees
27 Oct - 28 Oct
Underwater Cabana at Custom House Inn | On Duval!
A tranquil pond with a fountain in a park setting.

17. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The price is HK$1,664
HK$4,290 total
includes taxes & fees
27 Oct - 28 Oct
The Tortuga at Sunrise Suites - Balcony & Pool
A living room with a sofa, two chairs, a coffee table, a TV, and a ceiling fan.

18. Hollinsed House Studio - Great Location!!

Hollinsed House Studio - Great Location!!
Old Town Key West
9.6 out of 10, Exceptional, (162 reviews)
"Nice location, clean, & would stay there again"
United States
Karen L.
Hollinsed House Studio - Great Location!!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

19. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (113 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
The price is HK$926
HK$2,336 total
includes taxes & fees
20 Oct - 21 Oct
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A hot tub with a view of a marina and boats during sunset.

20. 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$3,296
HK$4,132 total
includes taxes & fees
20 Oct - 21 Oct
Living the Dream Key West Style
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dredgers Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Staff was great"
Robert A 3-night trip
Posted 12 hours ago
DoubleTree Resort by Hilton Grand Key - Key West

Find out more about Dredgers Key

Search for holiday rentals in Dredgers Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Dredgers Key using one of the methods below:

  • View our selection of featured holiday rentals in Dredgers Key
  • Use the map to find apartments and other holiday homes in the Dredgers Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dredgers Key while they last

Look no further and take a look at our great range of rental properties in Dredgers Key!

Explore a world of travel with Expedia