Entire home

Sailfish Retreat | Pool & boating on Cudjoe

Choose dates to view prices

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.
A modern kitchen with a central island, stainless steel appliances, and a dining area with wooden chairs and a table.
A covered porch with a ceiling fan, white railings, and a view of a house and greenery.
A canal with boats, a wooden dock, and a flag.
A modern kitchen with white cabinets, a central island with bar stools, and a microwave above it.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms1488 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

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

Room options

About the neighborhood

Summerland Key

Located in Cutthroat Harbor Estates, this vacation home is within a 15-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. The vacation home includes a private pool, a kitchen, and a balcony.

What's nearby

  • Upper Sugarloaf Key - 9 min drive - 5.6 miles
  • Florida Keys Beaches - 10 min drive - 5.6 miles
  • Upper Sugarloaf Sound - 11 min drive - 6.4 miles
  • Lower Sugarloaf Sound - 14 min drive - 8.6 miles
  • Key West Visitors Center - 20 min drive - 13.8 miles

Getting around

  • Key West Intl. Airport (EYW) - 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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 3 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a coffee maker.

Similar properties

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
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • 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

  • Smoking not allowed

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

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in 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

  • This property welcomes pets
  • Service animals exempt from fees
  • Note from host: 1 dog under 20 lbs w/ manager approval & fee

Children and extra beds

Children allowed: ages 0-17

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 indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.

Property is also known as

68f7ab367ea62e00104cbfd5

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in Cutthroat Harbor Estates, close to Florida Keys Beaches, Upper Sugarloaf Key, and Sugarloaf Beach. You'll also find Venture Out Keys and Venture Key nearby.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 22 mi away (34 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.9 mi away (40-minute drive).

Sailfish Retreat | Pool & boating on Cudjoe Reviews

Reviews

10

Exceptional

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

Reviews

Verified review

10/10 Excellent

bware2124 w.

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