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Featured Cottages in Cudjoe Key

Our top choices for Cudjoe Key cottages

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (256)
"River boat houses, pool, kayak rentals. "
Old Wooden Bridge Resort and Marina

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (162)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"I will sum it up by saying it was ok. It was a place to stay, would I book it again? No"
Canal front, dockage, 2 bedroom, 2 bath

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 AU$547
includes taxes & fees
21 Aug - 22 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (152)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West

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

9.0 out of 10, Wonderful, (141)
"We had an excellent time , property was an excellent place for our vacation.We hope to come back next year"
Quaint cottage, pool, dockage just minutes to Key West!

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

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

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is AU$544
includes taxes & fees
22 Aug - 23 Aug
Charming cottages, dockage, pool, just minutes to Key West

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

9.6 out of 10, Exceptional, (39)
"My family had a great time. Enjoyed the sunrises and sunsets from the back porch overlooking the bay. Very peaceful and quiet. Everyone was very friendly and helpful. Wish we could have stayed longer. Would definitely stay at the trailer again. Loved the turtle decor."
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (189)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

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

8.6 out of 10, Excellent, (144)
"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. "
The price is AU$398
includes taxes & fees
28 Aug - 29 Aug
Cottage with Pool and Boat Dockage just minutes to Key West!

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

9.0 out of 10, Wonderful, (153)
"The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around."
Cottage with swimming pool and dockage, just minutes to Key West!

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

10.0 out of 10, Exceptional, (29)
"We really enjoyed the mini vacation in the Florida Keys."
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

9.6 out of 10, Exceptional, (12)
"Even if it was a short stay, we enjoyed it and will be staying here again in the future."
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (5)
"First timers and would definitely come back!! "
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

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

9.6 out of 10, Exceptional, (28)
"Glen, the owner was great. Terrific room and furnishings. "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

Waterfront Home

8.8 out of 10, Excellent, (168)
"Great price great location "
Waterfront Home

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

9.0 out of 10, Wonderful, (50)
"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

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

8.6 out of 10, Excellent, (49)
"It was perfect for what we needed. Clean, convenient and cozy."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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)
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

Frequently asked questions

How much do cottages in Cudjoe Key cost?
Cottages in Cudjoe Key range between AU$398 and AU$547 per night. These retreats offer a chance to get in tune with nature — at a price you can afford. This price was 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?
Choose from 79 cottages in Cudjoe Key. Whether you're taking a trip with the kids or organising a weekend retreat with your pals, Expedia will help you find the perfect place to immerse yourself in nature.
What is there to do in Cudjoe Key near my cottage?
Cudjoe Key has enough sights to keep you occupied for weeks (or months!), starting with Florida Keys Beaches. Sugarloaf Beach, Big Pine Key Flea Market and Blue Hole are other impressive attractions. If you're staying a while longer, Cook Island and Upper Sugarloaf Sound will add the finishing touches to your itinerary.