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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 69 Cottages in Cudjoe Key with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (191)
"Beautiful room overlooking the marina. Loved the rockers on the deck. "
The price is AED 694
AED 1,148 total
includes taxes & fees
17 Feb - 18 Feb
Old Wooden Bridge Resort and Marina
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

9.0 out of 10, Wonderful, (42)
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."
The price is AED 863
AED 1,630 total
includes taxes & fees
3 Mar - 4 Mar
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
Exterior detail

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

8.8 out of 10, Excellent, (60)
"We just love this place"
The price is AED 1,010
AED 1,817 total
includes taxes & fees
19 Feb - 20 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
The price is AED 735
AED 1,276 total
includes taxes & fees
23 Feb - 24 Feb
Cottage with Pool and Boat Dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!
Exterior

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

9.0 out of 10, Wonderful, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is AED 918
AED 1,630 total
includes taxes & fees
4 Mar - 5 Mar
Quaint cottage, pool, dockage just minutes to Key West!
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

9.2 out of 10, Wonderful, (67)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is AED 1,010
AED 1,817 total
includes taxes & fees
26 Feb - 27 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Property grounds

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (19)
"Our stay was very pleasant. Enjoyed the pool and paddle board courts. The unit was clean and comfortable. Jessica was super easy to reach and extremely responsive. "
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Waterfront Cozy Cottage with Boat Ramp & Dock!
Cozy Cottage dock for fishing, snorkeling, and relaxing.

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (54)
"Brother-in-law and I stayed for 3 nights for a quick fishing getaway. The property was perfect for our needs. The property manager was proactive and communicative. He even reached out the day of check-in to let us know an early check-in was available. The property was in a nice quiet area, but just close enough to Kiki's to hear the evening live music from the fantastic pier. Also, within walking distance to Kiki's for a quick bite and a drink after fishing.The property was extremely clean...
Waterfront Cozy Cottage with Boat Ramp & Dock!
Waterfront Home
View from the porch

Waterfront Home

8.8 out of 10, Excellent, (155)
"I wasn't expecting a 140 resort fee due before proceeding past the gate guard. The gate guard's response to my puzzled look was, "You were aware of the resort fee, right?" The fee is likely (at least I hope) embedded in the TOS. Moving on. The property permits pets but walking one's dog is prohibited. The properties are so small that one must walk a dog. Knowing this property was on a canal with open water access, I was not surprised that it needed some TLC. I think, most folks rent this type...
The price is AED 918
AED 1,782 total
includes taxes & fees
21 Feb - 22 Feb
Waterfront Home
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Aerial view

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Drive to cottages

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

8.6 out of 10, Excellent, (38)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
The price is AED 863
AED 1,626 total
includes taxes & fees
8 Mar - 9 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (76)
"Cute house with wonderful features. Covered deck was a nice place to enjoy a book and meal. The open design of the living room and kitchen made the cottage feel big. The Venture Out community is welcoming. It was an excellent atmosphere to walk and bike in a safe space."
Canal front, dockage, 2 bedroom, 2 bath
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Riley's Retreat - Venture Out 107

Riley's Retreat - Venture Out 107

8.6 out of 10, Excellent, (7)
"We would stay here again. Very clean. Kitchen well supplied. The beds could be more comfortable, but that could be a preference of bed type. The blinds in the bedrooms did not close completly so if you sleep late the light could be an issue. Itwasnt for us."
Riley's Retreat - Venture Out 107
Direct Oceanfront Cottage-Sunrise View- #2,
Wouldn't you love to start your morning with a beautiful sunrise like this?

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
Cottage with swimming pool and dockage, just minutes to Key West!
Property grounds

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

9.0 out of 10, Wonderful, (138)
"We liked layout of cabins. Plenty of trees and brush provided a sense of privacy. Nice porchfor afternoon sitting. Close to lots of restaurants/bars with good seafood. "
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (132)
"We had a wonderful time at your place. Thank you for having us, we loved the Keys!"
Cottage with Pool and Dockage, just minutes to Key West
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

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

8.0 out of 10, Very Good, (33)
"This property is clean and adequate. Close to the lower keys, and easy to get to the upper keys and back. The listing indicates that there is a washer and dryer; however, these are coin-operated and in a different part of the compound, not in the unit. There has been road work done in the area, so the driveway was not easy to find by using the directions listed. All-in-all, not bad!"
The price is AED 643
AED 1,334 total
includes taxes & fees
24 Feb - 25 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Embrace tropical living at TURTLE COVE VIEWS...

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.4 out of 10, Exceptional, (30)
"The house was beautiful and right on the water! We didn't bring a boat so just sitting and having coffee every morning and night was awesome!! We did see several roaches in the kitchen but even in our own house of Florida we know all about them. The only part was we were getting ready to leave and packing our vehicle we left our four fishing rods right next to our vehicle and they were stolen. They really hurt us because 2 of them were custom and had names on them. Not sure who took them but we...
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
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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Other property types in Cudjoe Key

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

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

8.6 out of 10, Excellent, (106)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is AED 826
AED 1,516 total
includes taxes & fees
26 Feb - 27 Feb
Charming cottages, dockage, pool, just minutes to Key West
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Outdoor dining

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very Good, (99)
"Property was exaxtly as described. Could use some updating, but everything was clean and functioning. The house was plenty spacious, but we did spend most of out time on the deck. Wouod stay again! "
The price is AED 1,028
AED 2,222 total
includes taxes & fees
28 Feb - 1 Mar
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Relax on the little sandy beach.

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (223)
"Melanie gets top rating for being quick and thorough in responding to our questions or problems. The furniture was very comfortable and were the beds.The kitchen was well stocked with pot/pans/utensils and dishes but did not have an abundance of silverware so we had to run the dishwasher every day.Our biggest disappointment was the poor viewing of water. The ocean was only visible from the second third floor porch."
The price is AED 1,561
AED 3,329 total
includes taxes & fees
20 Feb - 21 Feb
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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.

Frequently asked questions

How much do cottages in Cudjoe Key cost?
Expect to pay between AED 694 and AED 1,010 per night for cottages in Cudjoe Key. No matter your budget, the perfect stay is only a few clicks away on Expedia. 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?
Reconnect with nature in one of the 69 cottages waiting for you in Cudjoe Key. To help you find an ideal place, make use of our filters to search for amenities or perks you prefer.
Why book your cottage in Cudjoe Key with Expedia?
Expedia has some superb cottages in Cudjoe Key, so get set for an unforgettable vacay on nature’s doorstep. If you’re on a budget, click on how much you’d like to spend and your preferred property star rating. Or, use our handy filters to search for cottages with a hot tub or a kitchen. We’ll help you find the perfect digs whatever your escape looks like.
How can I find cheap cottages in Cudjoe Key?
Expedia is here to help you locate cheap cottages in Cudjoe Key. To reserve your special stay in a few quick keystrokes, simply use our convenient filter tool to tailor your search results by star rating, amenities and budget.