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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Cudjoe Key and around

Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (253)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Waterfront Home
Enjoy stunning ocean views from the balcony of this beachfront property, featuring a spacious living area with large windows and comfortable outdoor seating.

Waterfront Home

8.8 out of 10, Excellent, (167)
"Great price great location "
Waterfront Home
Canal front, dockage, 2 bedroom, 2 bath
Relax by the pool surrounded by lush palm trees.

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"The place was everything as described. Close enough to Key West and beaches that we did not stay home much during the day but nice to have a peaceful place to land in the evenings. Bedrooms and bathrooms were right but served its purpose. Jennifer and Susan were very helpful with check in. Thanks for letting my parents relive their glory days in the Keys. I would stay again if we come back!"
Canal front, dockage, 2 bedroom, 2 bath
Direct Oceanfront Cottage-Sunrise View- #2,
Enjoy a tranquil beachside retreat with access to the calm sea and nearby amenities.

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (186)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Relax on the beach with lounge chairs and a tranquil sea view.

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

8.8 out of 10, Excellent, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
The price is €331
includes taxes & fees
4 Aug - 5 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (118)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is €281
includes taxes & fees
16 Aug - 17 Aug
Charming cottages, dockage, pool, just minutes to Key West
waterfront cottage near key west, sleeps 6
Enjoy waterfront views from the balcony of this two-story property, situated along a tranquil canal with a boat docked at the water's edge.

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (23)
"This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and"
waterfront cottage near key west, sleeps 6
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Relax by the beachside with picnic tables nestled among palm trees, overlooking a pool area or lounge.

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

9.6 out of 10, Exceptional, (38)
"Property was very clean and well stocked. Perfect location on the water. Would definitely rent again "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Cottage with Pool and Boat Dockage just minutes to Key West!
Enjoy an outdoor space with a swimming pool and lush greenery surrounding this two-story house.

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

8.6 out of 10, Excellent, (143)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Surrounded by lush greenery, this pool area offers a serene escape.

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (149)
"Good Fishing, Good local eateries. "
The price is €421
includes taxes & fees
5 Aug - 6 Aug
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Relax on the beach with lounge chairs and enjoy the tranquil ocean views.

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

9.0 out of 10, Wonderful, (49)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Enjoy a serene beachside picnic with a sailboat on the horizon.

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.6 out of 10, Exceptional, (27)
"It was an awesome time! Pool was nice and hot with an excellent location. Hope was a great hostess and look forward to coming back sooner than later "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Enjoy cooking in this well-equipped kitchen with a sink, stove, and dishwasher.

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

9.0 out of 10, Wonderful, (85)
"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "
The price is €438
includes taxes & fees
4 Aug - 5 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Quaint cottage, pool, dockage just minutes to Key West!
Guests can access the dock for a serene lakeside experience.

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

9.0 out of 10, Wonderful, (141)
"It is what it is, only wish the furniture was not worn out. "
Quaint cottage, pool, dockage just minutes to Key West!
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Enjoy waterfront dining and relaxation with a dock area, grill, and seating under a shaded umbrella.

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

9.8 out of 10, Exceptional, (129)
"We had a great vacation at this property. It's walking distance to the pool, hot tub and convenience store. The home had everything that we needed and was nicely decorated. Communication with the owner was excellent. "
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4
Guests can enjoy a serene beach scene with a clear view of the sea, walking paths, and scenic views.

PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4

9.8 out of 10, Exceptional, (47)
"Loved our stay at Palm Cottage!"
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Surrounded by palm trees and a body of water, this resort offers a tranquil atmosphere and a central swimming pool.

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

10.0 out of 10, Exceptional, (7)
"Property was clean, and staff were nice and helpful. Good location too"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Relax by the beach with picnic tables and a communal area under a green roof.

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

9.8 out of 10, Exceptional, (211)
"We had a great time staying here. House was perfect for us and the location was perfect to explore many of the keys! The bikes and kayaks that were provided were a great treat for the kids. We had fun biking around the village and swimming in the pool during down time. Would definitely stay here again! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Cozy, Perfect Conch Cottage! - VO315
Relax by the pool surrounded by palm trees and lounge chairs.

Cozy, Perfect Conch Cottage! - VO315

9.2 out of 10, Wonderful, (30)
"We had an amazing trip staying at cudjoe key. It’s a cute little trailer, very clean. The property was great. The renters are very attentive to questions. Highly recommend! "
Cozy, Perfect Conch Cottage! - VO315
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Enjoy the serene sea views from this balcony, featuring two lounge chairs and a palm tree in the distance.

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!

9.8 out of 10, Exceptional, (26)
"This was the perfect place to rent for a boat It was clean and had everything we needed"
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"Great stay away from downtown! "
Brigitte 1-night trip
Posted 19 hours ago
Hyatt Vacation Club at Windward Pointe, Key West

Frequently asked questions

How much do cottages in Cudjoe Key cost?
Rates for cottages in Cudjoe Key range between €281 and €438 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 holiday days and choose from 80 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 holiday 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.