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Sailfish Retreat | 3 bed, 2 bath canalfront home on Cudjoe Key
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Reviews
1010 out of 10
Exceptional
Entire home
Popular amenities
- Parking available
- Dryer
- Washer
- Pet friendly
- Kitchen
- Air conditioning
Explore the area

Cudjoe Key, FL
- Upper Sugarloaf KeyPlace, Upper Sugarloaf Key11 min drive
- Upper Sugarloaf SoundPlace, Upper Sugarloaf Sound12 min drive
- Florida Keys BeachesPlace, Florida Keys Beaches12 min drive
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)48 min drive
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$849 nightly
The price is $899
$899 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
About the neighborhood
Summerland Key
With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 15-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. .This vacation home is 16.1 mi (26 km) from Bahia Honda State Park and 8.8 mi (14.1 km) from Lower Sugarloaf Sound.
What's nearby
- Upper Sugarloaf Key - 11 min drive - 5.2 miles
- Upper Sugarloaf Sound - 12 min drive - 6.0 miles
- Florida Keys Beaches - 12 min drive - 5.0 miles
- Lower Sugarloaf Sound - 16 min drive - 8.4 miles
- Sugarloaf Beach - 23 min drive - 12.1 miles
Getting around
- Key West Intl. Airport (EYW) - 34 min drive
Restaurants
- Boondock's Grille & Drafthouse - 11 min drive
- Kiki's Sandbar - 13 min drive
- Morning Joint - 4 min drive
- 5 Brothers Two - 10 min drive
- Broil - 6 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 | 3 bed, 2 bath canalfront home on Cudjoe Key
Welcome to your perfect waterfront retreat on Cudjoe Key! This like-new 3 bedroom/2 bathroom monthly rental is situated on a boating canal with a short run to open water, offering you a slice of paradise with endless opportunities for relaxation and adventure.
As you step into the spacious living area, you'll immediately feel at home with a huge leather reclining sectional. The well-stocked kitchen and dining area, with seating for 4 at the table and 4 at the breakfast bar, make mealtime a breeze.
The three large bedrooms provide comfort and privacy in the following setup:
- King bed in the primary, with en-suite bath with soaking tub, separate shower and walk-in closet.
- Queen bed in the 2nd bedroom (shared full bath off hallway)
- 2 twin beds in the 3rd bedroom (shared full bath off hallway)
Step outside onto the covered porch to soak in the tropical atmosphere. Stay connected with high-speed Internet and WiFi. Bring your own streaming services or enjoy the offerings on the flat-screen smart TVs in the living area and each bedroom.
A ride down the canal from the concrete dock takes you to Cudjoe Bay and a 20-minute run to the reef, or take a short journey through Bow or Kemp channels, which open up the backcountry for your exploration. Cook your catch on the gas grill and dine al fresco in the shade. The boat lift (not pictured) and downstairs storage are for owner use only. There's room for a 25-foot boat at the dock.
Whether you're an angler or just looking for a serene waterfront escape, this monthly rental on Cudjoe Key is your gateway to the ultimate Florida Keys experience. Book now and create lasting memories in this waterfront paradise!
Cudjoe Key is a laid-back island just 22 miles away from the excitement of downtown Key West. Some of the best restaurants in the Lower Keys are found here, including the famous Square Grouper and island steakhouse Broil. There are public and private boat ramps nearby. A large grocery store is just a few miles away.
Please note: The primary guest must sign a rental agreement regardless of booking platform. This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking. One small dog permitted with $250 pet fee and manager approval. There's a cap on electric ($250) and water/sewer ($150).
As you step into the spacious living area, you'll immediately feel at home with a huge leather reclining sectional. The well-stocked kitchen and dining area, with seating for 4 at the table and 4 at the breakfast bar, make mealtime a breeze.
The three large bedrooms provide comfort and privacy in the following setup:
- King bed in the primary, with en-suite bath with soaking tub, separate shower and walk-in closet.
- Queen bed in the 2nd bedroom (shared full bath off hallway)
- 2 twin beds in the 3rd bedroom (shared full bath off hallway)
Step outside onto the covered porch to soak in the tropical atmosphere. Stay connected with high-speed Internet and WiFi. Bring your own streaming services or enjoy the offerings on the flat-screen smart TVs in the living area and each bedroom.
A ride down the canal from the concrete dock takes you to Cudjoe Bay and a 20-minute run to the reef, or take a short journey through Bow or Kemp channels, which open up the backcountry for your exploration. Cook your catch on the gas grill and dine al fresco in the shade. The boat lift (not pictured) and downstairs storage are for owner use only. There's room for a 25-foot boat at the dock.
Whether you're an angler or just looking for a serene waterfront escape, this monthly rental on Cudjoe Key is your gateway to the ultimate Florida Keys experience. Book now and create lasting memories in this waterfront paradise!
Cudjoe Key is a laid-back island just 22 miles away from the excitement of downtown Key West. Some of the best restaurants in the Lower Keys are found here, including the famous Square Grouper and island steakhouse Broil. There are public and private boat ramps nearby. A large grocery store is just a few miles away.
Please note: The primary guest must sign a rental agreement regardless of booking platform. This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking. One small dog permitted with $250 pet fee and manager approval. There's a cap on electric ($250) and water/sewer ($150).
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Guests will find features like internet access and onsite parking.
Property amenities
Internet
- Available in the house: Free WiFi
Parking and transportation
- Car required
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Ice maker
- Kitchen island
- Microwave
- Oven
- Refrigerator
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- 3 bedrooms
- Bedsheets provided
Bathroom
- 2 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- Smart TV
Outdoor areas
- Balcony
- Gas grill
Laundry
- Laundry facilities
- Washing machine
Comfort
- Air conditioning
Pets
- Pet friendly
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Iron/ironing board
Location highlights
- Near the sea
- 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
- Deadbolt lock
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
Pets 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
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, a first aid kit, and a deadbolt lock
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
We should mention
A car is required for transportation to and from this property
Property is also known as
c6ca5a89-9e88-4f36-9e54-986367a182ed