Entire home
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





Entire home
3 bedrooms2 bathrooms98 sq m
Popular amenities
- Pool
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
- Outdoor space
Explore the area

Cudjoe Key, FL
- Upper Sugarloaf KeyPlace, Upper Sugarloaf Key8 min drive
- Florida Keys BeachesPlace, Florida Keys Beaches9 min drive
- Upper Sugarloaf SoundPlace, Upper Sugarloaf Sound9 min drive
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)41 min drive
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About the area
Summerland Key
With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. .This vacation home is 15.8 mi (25.4 km) from Bahia Honda State Park and 8.4 mi (13.5 km) from Lower Sugarloaf Sound.
What's nearby
- Upper Sugarloaf Key - 8 min drive - 8.2 km
- Florida Keys Beaches - 9 min drive - 8.3 km
- Upper Sugarloaf Sound - 9 min drive - 9.5 km
- Lower Sugarloaf Sound - 12 min drive - 13.1 km
- Key West Visitors Center - 19 min drive - 21.6 km
Getting around
- Key West Intl. Airport (EYW) - 33 min drive
Restaurants
- Boondock's Grille & Drafthouse - 9 min drive
- Morning Joint - 3 min drive
- Kiki's Sandbar - 12 min drive
- Mangrove Mama's - 8 min drive
- Square Grouper Bar and Grill - 4 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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' seawall (maximum 36' boat/trailer)
- 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.
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' seawall (maximum 36' boat/trailer)
- 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.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. There's a private balcony. A kitchen is outfitted with a refrigerator, a microwave, and a dishwasher. Conveniences include a coffee/tea maker and a washing machine.
Guests will find features like internet access and onsite parking.
Property amenities
Pool/Spa
- Private pool
Internet
- Available in the house: WiFi
Parking and transport
- Parking on site
Kitchen
- Coffee/tea maker
- Dishwasher
- Microwave
- Refrigerator
Bedrooms
- 3 bedrooms
Bathroom
- 2 bathrooms
- Bathtub or shower
- Shower
Entertainment
- TV
Outdoor areas
- Balcony
- Barbecue grill
Laundry
- Laundry facilities
- Washing machine
Comfort
- Air conditioning
Pets
- No pets allowed
Suitability/Accessibility
- Smoke-free property
Services and conveniences
- Iron/ironing board
Location highlights
- On the waterfront
Safety features
- Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
- Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
General
- Unit size: 1,056 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed
Children and extra beds
Children are welcome
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property is also known as
16096
Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage Reviews
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