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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

Old Wooden Bridge Resort and Marina
Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Interior

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!
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!
Interior

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

3.0 star property
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Interior

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Good detailed check in info and property info. Clean. Upstairs bath had standing water while showering. Bed downstairs very uncomfortable. Pool was nice but cold. "
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Beach

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3.0 star property
9.0 out of 10, Wonderful, (2)
"Easy access to Smathers Beach across the street. Great location for families with children. "
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Outdoor dining

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3.0 star property
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Cottage by the Pool by Avantstay w/ Balcony, BBQ & Shared Pool! Month Long Stays Only
Interior

Cottage by the Pool by Avantstay w/ Balcony, BBQ & Shared Pool! Month Long Stays Only

3.5 star property
Cottage by the Pool by Avantstay w/ Balcony, BBQ & Shared Pool! Month Long Stays Only
Bogey's Retreat by Avantstay Golfer's Retreat w/ Shared Pool! Month Long Stays Only
Interior

Bogey's Retreat by Avantstay Golfer's Retreat w/ Shared Pool! Month Long Stays Only

3.0 star property
Bogey's Retreat by Avantstay Golfer's Retreat w/ Shared Pool! Month Long Stays Only
Cozy Key West Beach Cottage: Walk to Beaches!
Interior

Cozy Key West Beach Cottage: Walk to Beaches!

3.0 star property
Cozy Key West Beach Cottage: Walk to Beaches!
Place to Relax by Avantstay Shared Pool 3 Miles to Smather's Beach Month-long Stays Only
Interior

Place to Relax by Avantstay Shared Pool 3 Miles to Smather's Beach Month-long Stays Only

3.0 star property
Place to Relax by Avantstay Shared Pool 3 Miles to Smather's Beach Month-long Stays Only
Paradise Point by Avantstay Golf Course Living
Interior

Paradise Point by Avantstay Golf Course Living

3.0 star property
Paradise Point by Avantstay Golf Course Living
Gated Golf Community w/ Pool, Prime Location Mins to Old Town Long-term Stays
Interior

Gated Golf Community w/ Pool, Prime Location Mins to Old Town Long-term Stays

3.0 star property
Gated Golf Community w/ Pool, Prime Location Mins to Old Town Long-term Stays
Sea Glass Secrets by Avantstay 3 Mins to Beach
Interior

Sea Glass Secrets by Avantstay 3 Mins to Beach

3.0 star property
Sea Glass Secrets by Avantstay 3 Mins to Beach
Coral Breeze by Avantstay Close to Beach w/ Balcony & Shared Pool! Month Long Stays Only
Interior

Coral Breeze by Avantstay Close to Beach w/ Balcony & Shared Pool! Month Long Stays Only

3.5 star property
Coral Breeze by Avantstay Close to Beach w/ Balcony & Shared Pool! Month Long Stays Only
Casa de Rosalie by Avantstay Great Location w/ Pool, BBQ & Outdoor Dining Month Long Stays Only
Interior

Casa de Rosalie by Avantstay Great Location w/ Pool, BBQ & Outdoor Dining Month Long Stays Only

3.0 star property
Casa de Rosalie by Avantstay Great Location w/ Pool, BBQ & Outdoor Dining Month Long Stays Only
Dune Wind South by Avantstay Communal Pool & Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only
Beach

Dune Wind South by Avantstay Communal Pool & Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only

3.0 star property
Dune Wind South by Avantstay Communal Pool & Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only
Key West Home on Golf Course w/ Patio & Grill!
Interior

Key West Home on Golf Course w/ Patio & Grill!

3.0 star property
Key West Home on Golf Course w/ Patio & Grill!
Dock + Balcony: Serene Big Coppitt Key Escape
Outdoor pool

Dock + Balcony: Serene Big Coppitt Key Escape

3.0 star property
Dock + Balcony: Serene Big Coppitt Key Escape
Waterfront Key West Oasis w/ Float Dock!
Interior

Waterfront Key West Oasis w/ Float Dock!

3.0 star property
Waterfront Key West Oasis w/ Float Dock!
Angler's Oasis w/ Boat Dock in Big Pine Key!
Interior

Angler's Oasis w/ Boat Dock in Big Pine Key!

3.0 star property
Angler's Oasis w/ Boat Dock in Big Pine Key!
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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Frequently asked questions

How much do cottages in Cudjoe Key cost?
Rates for cottages in Cudjoe Key range between and 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 23 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.