Blackbeard's Hideaway | Cozy Cudjoe cottage | House in Summerland Key

Summary:
Oceanside monthly rental with dock, bait freezer, fish-cleaning station, and easy open-water access — ideal for anglers and extended Florida Keys stays.
The Space:
Welcome to Blackbeard’s Hideaway — a laid-back, oceanside retreat designed for extended stays in the heart of Cudjoe Key. Tucked into a quiet neighborhood, this inviting waterfront home offers the perfect blend of island comfort, boating convenience, and relaxed coastal living.
Inside, an open and airy floor plan welcomes you with warm pine floors, vaulted ceilings, and two distinct living areas — ideal for spreading out, entertaining, or simply unwinding after a day on the water. The updated kitchen features sleek stainless appliances and quartz countertops, making everything from casual breakfasts to sunset dinners a pleasure.
The main level includes two king bedrooms, thoughtfully furnished for comfort and restful nights, along with a shared bathroom. A spiral staircase leads to a cozy open loft with a full-size bed — a perfect hideaway for additional guests. The great room also has a comfortable fold-out sofa, plus a convenient half bath off the living area.
Outdoor living truly shines at Blackbeard’s Hideaway. A wrap-around covered porch, accessible from every room, invites you to enjoy gentle sea breezes all winter long. Boaters and anglers will appreciate 60 feet of concrete dockage, a swim ladder, outdoor shower with hot and cold water, fish-cleaning station, bait freezer, ice maker, gas grill and a fully fenced yard — everything you need for effortless Keys living.
Inside, stay connected with high-speed internet and smart TVs in the living room and both bedrooms. A lockable storage shed is also available for securing personal items or outdoor gear during your stay.
Whether you’re here to fish, boat, relax, or simply slow down and savor island life, Blackbeard’s Hideaway offers the space, comfort, and location to make your extended Keys escape unforgettable.
Important Notes & Rental Details
- Minimum 28-day stay required by Monroe County ordinance
- Primary guest must sign a rental agreement, regardless of booking platform
- Proper county and state taxes collected, regardless of booking platform
- Primary renter must be 25+ years old
- Maximum overnight occupancy: 6 guests
- No smoking on the property
- One small to medium dog permitted with manager approval and a $250 nonrefundable fee
- Utilities included with caps on usage of $300 for electric and $150 for water
Blackbeard’s Hideaway is ideal for guests seeking a longer-term oceanside stay — where boating days, porch evenings and true Keys relaxation come together effortlessly.
Guest Access:
Guests have the house to themselves.
The Neighborhood:
Cutthroat Harbor Estates, a residential neighborhood of mostly single-family homes, is on the ocean side of Cudjoe Key, an island 23 miles from Key West. The famous Square Grouper restaurant is nearby. There is a convenience store and two seafood markets on the island. The closest boat ramp is Cudjoe Marina in the Cudjoe Gardens neighborhood nearby.
Getting Around:
A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.
Interaction with Guests:
Contact-free checkin and checkout are available. We value our guests’ privacy but are always available if needed.

Blackbeard's Hideaway | Cozy Cudjoe cottage is located in Cutthroat Harbor Estates. Blackbeard's Hideaway | Cozy Cudjoe cottage provides accommodation, featuring Internet, Pet Friendly, Sports/Activities, among other amenities. This House features Internet, Pet Friendly, Sports/Activities, to make your stay a comfortable one.

Blackbeard's Hideaway | Cozy Cudjoe cottage has 2 Bedrooms , 1 Bathroom, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Cutthroat Harbor Estates has interesting places to visit. If you want to learn more about the House in Cutthroat Harbor Estates, such as places to visit and things to do nearby, you can check below to learn more.