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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 covered outdoor area with a pool, seating, and potted plants.
A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water.
A marina with multiple boats docked, surrounded by buildings and greenery.
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a large island with stools.
A waterfront property with a pool, a dock, and a covered outdoor seating area.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Balcony
  • Private pool
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪8 min drive‬
  • Place, Florida Keys Beaches
    ‪9 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪9 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪39 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Living Room

1 Queen Sofa Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony

Add dates for prices

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About the area

Summerland Key

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.
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Map
Cudjoe Key, FL

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 - 13 min drive - 13.1 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

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬3 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬10 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬7 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 does it cost to stay at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage?

As of 24 Oct 2026, prices found for a 1-night stay for 2 adults at Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage on 7 Sept 2027 start from £6,898, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 3 Oct 2026
Thank you so much for the wonderful review! We’re thrilled to hear that you loved the home and had such a great experience with the neighbors. It means so much to us to know you’re already planning to return for years to come! We look forward to welcoming you back again and again!
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