Search Cudjoe Key Cottage Rentals from CA $151

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Check prices for these dates

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

Browse Select Cudjoe Key Cottages

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
The price is CA $151
CA $365 total
includes taxes & fees
Aug 12 - Aug 13
Old Wooden Bridge Resort and Marina
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (167)
"Great price great location "
Waterfront Home
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

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,
On the beach

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,
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season
Pool

OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

9.4 out of 10, Exceptional, (28)
"Great private location"
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season
waterfront cottage near key west, sleeps 6
Marina

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (22)
"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
Outdoor dining

**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 Dockage, just minutes to Key West
Pool

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 CA $379
CA $655 total
includes taxes & fees
Aug 5 - Aug 6
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

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!
Beach

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
Beach nearby

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. "
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
Fridge, microwave, oven, stovetop

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 CA $344
CA $634 total
includes taxes & fees
Aug 1 - Aug 2
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4
Sun loungers, beach towels

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

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

9.0 out of 10, Wonderful, (140)
"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
Outdoor dining

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

**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
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, (6)
"Property was clean, and staff were nice and helpful. Good location too"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Cozy, Perfect Conch Cottage! - VO315
A heated pool

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
Beautiful Cottage & Amenities in Gated Community
A heated pool

Beautiful Cottage & Amenities in Gated Community

10.0 out of 10, Exceptional, (2)
"Beautiful home, perfect for our needs"
Beautiful Cottage & Amenities in Gated Community
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Property grounds

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

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront

10/10 Excellent
"Great service. Annette from check in desk was very friendly and welcoming. Rooms were big and had comfy beds."
Deepa 1-night trip
Posted 16 hours ago
Courtyard by Marriott Key West Waterfront

Frequently asked questions

How much do cottages in Cudjoe Key cost?
Rates for cottages in Cudjoe Key range between CA $151 and CA $379 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 79 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.