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Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage

Photo gallery for Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage

A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water. - Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage (Cudjoe Key)
A covered outdoor area with a pool, seating, and potted plants. - Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage (Cudjoe Key)
A beach with palm trees, a sandy shore, and a calm sea under a partly cloudy sky. - Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage (Cudjoe Key)
A waterfront property with a pool, a dock, and a covered outdoor seating area. - Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage (Cudjoe Key)
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a large island with stools. - Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage (Cudjoe Key)
Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage provides laundry facilities and more. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

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About this property

Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage

  • Welcome to Pirate’s Paradise – your ideal tropical escape in the Lower Keys!



    This 3-bedroom canal front home on Cudjoe Key offers the perfect mix of relaxation, adventure, and island charm.



    Step into a bright, breezy living space with coastal decor and an open layout that brings everyone together. The well-equipped kitchen makes meal prep a breeze, and the comfortable furnishings invite you to unwind after a day on the water.



    Outside, you’ll find a private heated and chilled pool for year-round comfort, surrounded by lush landscaping and space to soak up the sun or sip cocktails in the shade. Boaters will love the convenient dockage with easy access to both the Atlantic and the Gulf, making this the perfect home base for your Florida Keys adventures.



    Whether you’re reeling in the catch of the day, exploring nearby islands, or simply enjoying canal views and island breezes, Pirate’s Paradise is your ultimate Cudjoe Key retreat.



    SLEEPS MAXIMUM OF 6 GUESTS:



    Bedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV)



    Bedroom 2: Queen Bed, Smart TV (no cable/satellite TV)



    Bedroom 3: Queen Bed, Smart TV (no cable/satellite TV)



    Living Room: Sofa W/ Pull Out Queen Bed, Two Chairs, Smart TV (no cable/satellite TV)



    Kitchen: Nicely equipped (all things necessary to prepare and serve a meal)



    AMENITIES:



    - 60' Waterfront, Maximum Boat Length 35'



    - Private Heated/Chilled Saltwater Pool (heated/chilled to ~85-87 degrees)



    - Outdoor Seating



    - Propane BBQ Grill



    - Linen's and towels provided



    - Parking for up to 4 vehicles, including boat trailers. RV's are not permitted.



    IMPORTANT POLICIES FOR YOUR STAY:



    Minimum Rental Period: County of Monroe zoning requires a minimum rental period of 28 nights, and no exceptions can be made.



    Age and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing.



    No Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors.



    No Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process.



    Boating Safety: Due to bridges and varying water depths, it is your responsibility to verify that your boat can safely navigate the local waters, access the canal, and fit the listed dockage before booking this property. Please ensure that your boating activities are conducted safely and in compliance with local regulations.



    Wildlife & Pest Advisory: The Florida Keys are home to various insects, including mosquitoes, no-see-ums, termites, etc. While routine pest control is in place, complete elimination is not possible. Additionally, guests may encounter geckos, lizards, iguanas, frogs, and chickens, which are part of the natural environment. We encourage guests to take necessary precautions, such as using insect repellent and keeping doors closed, to minimize exposure. Enjoy the beauty of the Keys with an understanding of its unique ecosystem!



    Construction Notice: The Florida Keys are resort islands where renovations, new construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by construction in the area.



    Image Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and owners frequently update their properties. Additionally, photos are taken in different lighting conditions, and screen settings may affect how colors appear. For the most accurate information, please refer to the written description and feel free to reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

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About the area

Located on the waterfront, this holiday home is in Cutthroat Harbor Estates, a neighbourhood in Summerland Key. Florida Keys Beaches and Upper Sugarloaf Key reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Visit our Summerland Key travel guide
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Map
Cudjoe Key, FL

What's nearby

  • A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.
    Florida Keys Beaches
    9 min drive - 8.3 km
  • A thatched-roof outdoor seating area with tables and chairs overlooking a body of water.
    Lower Sugarloaf Sound
    13 min drive - 13.1 km
  • Upper Sugarloaf Key
    8 min drive - 8.2 km
  • Upper Sugarloaf Sound
    9 min drive - 9.5 km
  • National Key Deer Refuge Visitor Center
    17 min drive - 19.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.)
    33 min drive

Restaurants

  • Morning Joint
    3 min drive
  • Kiki's Sandbar
    12 min drive
  • Boondock's Grille & Drafthouse
    9 min drive
  • Tonio's Seafood Shack & Tiki Bar
    7 min drive
  • Square Grouper Bar and Grill
    4 min drive

Frequently asked questions

Is Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage pet-friendly?

No, pets are not allowed at this property.

How much is parking at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

On-site parking is available at the property.

What time is check-in at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

Check-in begins at 4:00 PM.

What time is check-out at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

Checkout is at 10:00 AM.

Where is Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage located?

Located in Cutthroat Harbor Estates, this holiday home is within 6 miles (10 km) of Upper Sugarloaf Key, Florida Keys Beaches and Boondocks Grille & Draft House. Lower Sugarloaf Sound and Big Pine Key Flea Market are also within 9 miles (15 km).

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Reviews

Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely an amazing home and the neighbors on all side are amazing definitely will rent for years to come!
Stayed 30 nights in Jul 2026