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Sailfish Retreat | Pool & boating on Cudjoe

Photo gallery for Sailfish Retreat | Pool & boating on Cudjoe

An aerial view of a coastal resort with multiple buildings, clear blue waters, and a small island in the background. - Sailfish Retreat | Pool & boating on Cudjoe (Cudjoe Key)
A covered porch with a ceiling fan, white railings, and a view of a house and greenery. - Sailfish Retreat | Pool & boating on Cudjoe (Cudjoe Key)
A modern kitchen with white cabinets, a central island with bar stools, and a microwave above it. - Sailfish Retreat | Pool & boating on Cudjoe (Cudjoe Key)
A canal with boats, a wooden dock, and a flag. - Sailfish Retreat | Pool & boating on Cudjoe (Cudjoe Key)
A modern kitchen with a central island, stainless steel appliances, and a dining area with wooden chairs and a table. - Sailfish Retreat | Pool & boating on Cudjoe (Cudjoe Key)
Sailfish Retreat | Pool & boating on Cudjoe provides laundry facilities and more. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms138 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Add dates for prices

About this property

Sailfish Retreat | Pool & boating on Cudjoe

  • Summary:

    Settle into island life at Sailfish Retreat, a 3-bedroom, 2-bathroom canalfront home on Cudjoe Key. Enjoy a private pool, covered outdoor living and concrete dockage for a boat up to 25 feet. With quick boating access to Cudjoe Bay, the reef and backcountry, it’s an ideal monthly escape for boaters, anglers and families.



    The Space:

    Welcome to Sailfish Retreat, your waterfront escape on Cudjoe Key! This like-new 3-bedroom, 2-bathroom monthly rental sits on a boating canal with a short run to open water. A private pool (photos to come) between the house and canal creates an inviting place to cool off, relax and enjoy the tropical waterfront setting.



    Comfortable Island Living

    Inside, the spacious living area features a large leather reclining sectional with plenty of room to unwind. The well-stocked kitchen and dining area offer seating for four at the table and four at the breakfast bar, making meals at home easy and comfortable.



    Sleeping Arrangements

    - The primary bedroom has a king bed, walk-in closet and en-suite bathroom with a soaking tub and separate shower.

    - The second bedroom has a queen bed and access to the shared hallway bathroom.

    - The third bedroom has two twin beds and access to the shared hallway bathroom.



    Pool and Outdoor Living

    Step onto the covered porch to enjoy views of the pool and canal. Take a refreshing swim, relax poolside or cook your catch on the gas grill and dine outdoors in the shade. Please be aware that the private pool is not heated.



    Stay Connected

    High-speed internet and WiFi make it easy to stay connected. Bring your own streaming services to enjoy on the flat-screen smart TVs in the living area and each bedroom.



    Bring Your Boat

    A ride down the canal from the concrete dock takes you to Cudjoe Bay, with approximately a 20-minute run to the reef. Bow and Kemp channels also provide access to the backcountry for fishing and exploring.

    There is room for a boat up to 25 feet at the dock. The boat lift, which is not pictured, and downstairs storage are reserved for owner use only.



    Explore Cudjoe Key

    Cudjoe Key is a laid-back island approximately 22 miles from downtown Key West. Some of the Lower Keys’ most popular restaurants are nearby, including Square Grouper and the island steakhouse Broil. Public and private boat ramps are available in the area, and a large grocery store is just a few miles away.

    Whether your ideal Keys stay includes fishing, boating, relaxing beside the pool or simply enjoying the waterfront, Sailfish Retreat offers a comfortable home base for a month or longer in the Lower Keys.



    Good to Know

    - This home requires a minimum 28-day stay per Monroe County ordinance.

    - The primary guest must sign a rental agreement regardless of booking platform.

    - Proper county and state taxes are collected regardless of booking platform.

    - The primary renter must be 25 or older.

    - Overnight occupancy is limited to a maximum of six people. All overnight guests must be registered with the property manager.

    - One small to medium dog is permitted with manager approval and a $250 nonrefundable pet fee.

    - Electric usage is capped at $300 and water/sewer usage is capped at $200. Any overages will be billed to the guest.

    - The private pool is not heated.

    - No smoking is permitted.

Property amenities

Pool/Spa

  • Communal pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,488 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
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 are allowed
Service animals are welcome, and are exempt from fees
Note from host: 1 dog under 20 lbs w/ manager approval & fee

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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
View more Holiday homes in Summerland Key
Map
Cudjoe Key, FL

What's nearby

  • A beach with a pier extending into the ocean during sunset.
    Florida Keys Beaches
    10 min drive - 9.0 km
  • A thatched-roof outdoor seating area with tables and chairs overlooking a body of water.
    Lower Sugarloaf Sound
    14 min drive - 13.8 km
  • Upper Sugarloaf Key
    9 min drive - 8.9 km
  • Upper Sugarloaf Sound
    11 min drive - 10.2 km
  • National Key Deer Refuge Visitor Center
    18 min drive - 20.6 km

Getting around

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

Restaurants

  • Boondock's Grille & Drafthouse
    11 min drive
  • Morning Joint
    4 min drive
  • Kiki's Sandbar
    13 min drive
  • Looe Key Tiki Bar & Restaurant
    11 min drive
  • Square Grouper Bar and Grill
    5 min drive

Frequently asked questions

Does Sailfish Retreat | Pool & boating on Cudjoe have a pool?

Yes, this property has a pool.

Is Sailfish Retreat | Pool & boating on Cudjoe pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Sailfish Retreat | Pool & boating on Cudjoe?

Check-in begins at 4:00 PM.

What time is check-out at Sailfish Retreat | Pool & boating on Cudjoe?

Checkout is at 10:00 AM.

Where is Sailfish Retreat | Pool & boating on Cudjoe 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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Sailfish Retreat | Pool & boating on Cudjoe Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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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

Cleanliness

10

Location

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great quiet spot

House was clean and in great shape when we arrived. Great access to Cudjoe Bay, lots of fish in the canal and around the boat docks in the bay. Convenient location between Key West and Marathon.
Stayed 28 nights in Feb 2025