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Our top choices for Dredgers Key cottages

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
Quaint cottage, pool, dockage just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Bad need of repair....rust....no boat ramp......shallow water....screened in porch was aweful with holes in the screens and lots of mosquitos and rusted grill."
United States
Debra M.
$257 nightly
The price is $285
Dec 22 - Dec 23
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (29)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very Good, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (90)
"Nice place to vacation "
United States
Kevin D.
$312 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Living Life Dockside

Living Life Dockside
Stock Island
$513 nightly
The price is $570
Jan 4 - Jan 5, 2026
Total with taxes and fees
Living Life Dockside

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (75)
"Place was everything we needed, would definitely stay again "
United States
James h.
$312 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$315 nightly
The price is $349
Dec 27 - Dec 28
Total with taxes and fees
Cottage with swimming pool and dockage, just minutes to Key West!

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
$297 nightly
The price is $330
Dec 22 - Dec 23
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
Cottage with Pool and Dockage, just minutes to Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (54)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
$627 nightly
The price is $686
Dec 24 - Dec 25
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4

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
9.6 out of 10, Exceptional, (10)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
$673 nightly
The price is $747
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (26)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (10)
"Great place to stay! "
United States
sarah R.
$888 nightly
The price is $976
Dec 24 - Dec 25
Total with taxes and fees
Find your zen at HIDDEN TREASURE

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (96)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
United States
Kathryn W.
$966 nightly
The price is $1,064
Jan 17 - Jan 18, 2026
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval
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

Find out more about Dredgers Key

Dredgers Key Cottages information

Number of reviews
1,298
Accommodation
95 Cottages
Lowest Price
$285
Highest Price
$1,064

Frequently asked questions

How much do cottages in Dredgers Key cost?
Rates for cottages in Dredgers Key range between $285 and $1,064 per night. Whatever your budget, you're sure to find a perfect place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Dredgers Key?
A traveler favorite is Simonton Court Cottages. Rest easy at this 3-star stay which features WiFi and a fridge. Casa Manana Key West Monthly: 2 Br is another popular option to look into. Spend your vacation at this 3-star cottage and make the most of amenities like a garden and a barbecue grill. There are multiple cottages in Dredgers Key with a total average guest review rating of 9.2.
How many cottages are there in Dredgers Key?
Enjoy reconnecting with nature in one of the 95 cottages on offer in Dredgers Key. To help you reserve a stay that's right for you, make use of our handy filters to search for must-have amenities.
Are there any family-friendly cottages in Dredgers Key?
Get cozy at Simonton Court Cottages, a 3-star cottage not far from downtown. Conveniences here include WiFi and housekeeping services. Another family-friendly option where you can swap the urban jungle for fresh air and nature is Casa Manana Key West Monthly: 2 Br. An oven and clothes washing facilities help make this 3-star cottage a hit with guests. Once you've checked in, there are lots of family-friendly attractions to visit around Dredgers Key. Smathers Beach and South Beach are two of our top picks.
Why book your cottage in Dredgers Key with Expedia?
Booking a cottage in Dredgers Key is as simple as deciding on your travel dates and choosing an ideal place for outdoor relaxation and recreation. From luxurious retreats to affordable properties and cottages that come with perks like a pool, Expedia has something for all tastes. As for the best offers around? We've got them too!
How can I find cheap cottages in Dredgers Key?
The simplest way to compare cheap cottages in Dredgers Key is with Expedia's user-friendly filter tool. Narrow your search results by star rating, budget and amenities to secure unbeatable rates in just a few keystrokes.

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