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Compare 62 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, (161)
"Loved this stay!!! May not be for everyone but we loved the rustic feel and being away from the crowds!!! The staff was very friendly and our cabin on the water was comfy and cozy! Would definitely stay again. "
The price is SAR 484
SAR 920 total
includes taxes & fees
26 Nov - 27 Nov
Old Wooden Bridge Resort and Marina
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, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
waterfront cottage near key west, sleeps 6
pools, a spa and the ocean, what more do you need?

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
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, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225

Blue Mind - Venture Out Unit 225

9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Welcome to Tidewater Views...

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

10.0 out of 10, Exceptional, (200)
"Great little place on the water especially if you are bringing a boat. The house was perfect! It was my birthday and our host Charity even got me a birthday cake and card. We will definitely be back!! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
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, (51)
"I really enjoyed it there we / my 12 year old and I . Took out charters everyday that we were there . They will pick you up from your dock ! We will be back .. Great experience!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
SEA SHELL COTTAGE UNIT #2
Welcome to Hidden Hammock

SEA SHELL COTTAGE UNIT #2

9.2 out of 10, Wonderful, (11)
"We thoroughly enjoyed our stay here, the room we rented was perfect for us it definitely has an old school vibe. The pool was nice on the hot summer days but they were going through a bit of a crab invasion while we were there. But that was no big deal for us. Hope was super nice and have a bunch of suggestions for things to do and places to eat while down there. Ask in all we had a great time and will try to return in the future."
SEA SHELL COTTAGE UNIT #2
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, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
PALM COTTAGE
Welcome to the Palm Cottage at Hidden Hammock

PALM COTTAGE

10.0 out of 10, Exceptional, (28)
"First time we had stayed in Summerland Key. Great place to stay. Close to everything we wanted to do. Due to Hurricane Milton we decided to cut our visit short. Trina and Hope were very accommodating with our needs!! We will be back "
PALM COTTAGE
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
Ocean Breeze House Sleeps 7. Two bedrooms two bathrooms

OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK

9.4 out of 10, Exceptional, (15)
"We loved the area Hope wad great and wr had a great time!"
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Star Fish Cottage - pool entrance

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
FL Keys Cottage with Ocean Views - Venture Out Unit 395

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
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, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Waterfront Home
View from the porch

Waterfront Home

8.8 out of 10, Excellent, (150)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (73)
"Property was just as advertised and looked as nice in person as in ads"
Canal front, dockage, 2 bedroom, 2 bath
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

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

9.6 out of 10, Exceptional, (10)
"Our stay was wonderful! The room was perfect for our stay. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
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, (10)
"It was great. Very unique place. I will def be back with the pet’s next time. 5 stars"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
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, (15)
"awesome place"
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Exterior

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

10.0 out of 10, Exceptional, (5)
"Took my grandmother on her bucket list trip. Great location and set up for myself, my mom and grandmother!"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
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

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
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, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is SAR 1,032
SAR 2,691 total
includes taxes & fees
26 Nov - 27 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Exterior

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (198)
"The location was perfect and the unit was clean and comfortable. The key lime pie from the hosts was a nice touch."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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 SAR 484 and SAR 484 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 62 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.