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Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Cudjoe Key cottages

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

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (90)
"Nice place to vacation "
United States
Kevin D.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage in Cudjoe Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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 21 - Dec 22
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior
Charming cottages, dockage, pool, just minutes to Key West

Cottage in Cudjoe Key

Charming cottages, dockage, pool, just minutes to Key West
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
$297 nightly
The price is $330
Dec 21 - Dec 22
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
Property grounds
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cottage in Cudjoe Key

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
9.6 out of 10, Exceptional, (12)
"The owners were fantastic to deal with and the house was great. "
United States
Anonymous traveler
$348 nightly
The price is $387
Dec 23 - Dec 24
Total with taxes and fees
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Exterior
Canal front, dockage, 2 bedroom, 2 bath

Cottage in Cudjoe Key

Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (89)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
$334 nightly
The price is $370
Dec 21 - Dec 22
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very Good, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage in Cudjoe Key

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

Cottage in Cudjoe Key

Quaint cottage, pool, dockage just minutes to Key West!
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$286 nightly
The price is $317
Dec 21 - Dec 22
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (75)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Cottage with Pool and Dockage, just minutes to Key West

Cottage in Cudjoe Key

Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$429 nightly
The price is $476
Dec 21 - Dec 22
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Exterior
Old Wooden Bridge Resort and Marina

Cottage in Punta Brisa

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (279)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
$241 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Marina
Living Life Dockside

Cottage in Stock Island

Living Life Dockside
$560 nightly
The price is $622
Jan 4 - Jan 5, 2026
Total with taxes and fees
Living Life Dockside
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 Cudjoe Key Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"The front desk staff was amazing. The hotel is clean and in a wonderful location. They offer a free shuttle to the main area near Duval Street which is super convenient. We would definitely stay here again. Oh and we were here celebrating my birthday and they left us a bottle of champagne and a cute card in our room, it totally made my day. "
JULIE 4-night trip
Posted 22 hours ago
Hilton Garden Inn Key West / The Keys Collection

Find out more about Cudjoe Key

Cudjoe Key Cottages information

Number of reviews
1,387
Accommodation
89 Cottages
Lowest Price
$271
Highest Price
$622

Frequently asked questions

How much do cottages in Cudjoe Key cost?
Rates for cottages in Cudjoe Key range between $271 and $622 per night. Whatever your budget, you're sure to find an ideal place to get in touch 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.
How many cottages are there in Cudjoe Key?
Take advantage of your vacation days and choose from 89 cottages in Cudjoe Key. Looking for a place where you can relax and stay in touch with nature? Expedia will help you find your ideal stay in just a few clicks.
Why book your cottage in Cudjoe Key with Expedia?
Expedia has some wonderful cottages in Cudjoe Key, so get set for a memorable vacay close to nature. If you're on a budget, click on how much you're willing to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect digs whatever your style of travel or plans.
How can I find cheap cottages in Cudjoe Key?
A wonderful way to spot cheap cottages in Cudjoe Key is with Expedia's user-friendly filter tool. Refine your search by star rating, amenities and budget to snag awesome rates in a couple of clicks.

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