Entire home

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

Summerland Key vacation home in Cutthroat Harbor Estates area

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Marina
TV
Beach
Fridge, microwave, dishwasher, coffee/tea maker
Pool

Entire home

3 bedrooms2 bathrooms1056 sq ft

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pool
  • Barbecue grill
  • Air conditioning

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Venture Out Keys
  • Place, Upper Sugarloaf Key
    ‪10 min drive‬
  • Place, Florida Keys Beaches
    ‪12 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪46 min drive‬

Room options

About the neighborhood

Summerland Key

Cutthroat Harbor Estates stay.Your stay at this Cutthroat Harbor Estates vacation home places you within 6 miles (10 km) of Upper Sugarloaf Key and Florida Keys Beaches. Also within 9 miles (15 km) are Lower Sugarloaf Sound and Big Pine Key Flea Market.

What's nearby

  • Upper Sugarloaf Key - 10 min drive - 4.7 miles
  • Florida Keys Beaches - 12 min drive - 5.3 miles
  • Sugarloaf Beach - 22 min drive - 11.6 miles
  • Bahia Honda State Park - 39 min drive - 20.6 miles
  • Boca Chica Nude Beach - 42 min drive - 19.8 miles

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪5 Brothers Two - ‬9 min drive
  • ‪Morning Joint - ‬3 min drive
  • ‪Broil - ‬5 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.

Similar properties

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Internet access

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

  • Smoking not allowed

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

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.

Property is also known as

16096

Frequently asked questions

How close is Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage to the airport?

This vacation home is 21.6 mi (33-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage to the beach?

This vacation home is 4.3 mi (10-min drive) from Florida Keys Beaches and 11.4 mi (23-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

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

This vacation home does not offer free breakfast.

Is there a casino at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

No, there is no casino at this vacation home.

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.

Is there free parking at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

Free parking is not available at this vacation home.

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

Yes, there's a private pool.

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

There are no spa services available at this vacation home.

How close is Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage to downtown Summerland Key?

This vacation home is 2.1 mi away from Summerland Key.

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