Entire home

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Waterfront holiday home with kitchen and balcony

Photo gallery for Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Castaway - Sugarloaf Key
Property grounds
Terrace/patio
Kitchen
Dining Room

Reviews

9.2 out of 10
Wonderful
4 bedrooms3 bathroomsSleeps 122100 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Pet-friendly
  • Barbecue grill

Explore the area

View in a map
  • Place, Upper Sugarloaf Sound
  • Place, Upper Sugarloaf Key
  • Place, Florida Keys Beaches
  • Airport, Key West, FL (EYW-Key West Intl.)

Rooms & beds

4 bedrooms (sleeps 12)

Family Room - Downstairs

1 Single Bed, 1 Queen Bed and 1 Double Bed

Guest Bedroom

1 Queen Bed

Guest Bedroom

1 Double Bed and 1 Single Bed

Master Bedroom

1 King Bed

3 bathrooms

Downstairs Bathroom

Toilet · Outdoor shower

Guest Bathroom

Bathtub or shower · Toilet · Jetted bathtub

Master Bathroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Balcony
Separate dining area
Outdoor play area
Dining area

About this property

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Castaway – Your Ultimate Vacation Home on Sugarloaf Key

Welcome to Castaway, a stunning 4-bedroom, 3-bathroom vacation home perfectly situated on a large corner double lot in a private cul-de-sac on Sugarloaf Key. This is a getaway like no other—surrounded by uninterrupted panoramic views of the Gulf of Mexico, where water stretches as far as the eye can see.

Unmatched Location & Privacy
Enjoy the privacy of no neighbors on three sides and ample space for your boats, water toys, and vehicles. With your own 10-ton boat lift accommodating vessels up to 26’ and 6,500 lbs, a dock with a fish cleaning station, outdoor power, and a boat basin for kayaks and other watercraft, this is a water enthusiast’s dream come true.

Light-Filled, Spacious Interior
The home’s interior boasts oversized floor-to-ceiling windows, flooding the space with natural light and framing breathtaking Gulf views from every room. The open-concept kitchen and dining area are designed for both comfort and entertainment, featuring a gas range stove, breakfast nook, dining table for six, and a breakfast bar with stools.

Living Spaces Designed for Relaxation

Living Room: Relax on the sectional couch and recliner while watching your favorite shows on the 50” flat-screen TV.

Master Bedroom: A spacious retreat with a king-size bed, ample closet and storage space, chest of drawers, en-suite bathroom with shower, and spectacular Gulf views from four large windows.

Bedroom 2: Queen-size bed, flat-screen TV, large closet, and dresser.

Bedroom 3: Oversized room with one full-size bed, one single bed, and an organizer-equipped closet.

Bedroom 4 (Bonus Room): Downstairs family room featuring bunk beds (single over full), queen bed, and sofa sleeper. Note: This room is included only for groups of 9 or more; additional charges apply.

Bathrooms:

Master bath with full shower

Shared full bath with oversized jet jacuzzi bathtub/shower combo

Downstairs half bath with an outdoor shower

Outdoor Living & Entertainment
A partial wrap-around deck offers outdoor dining and sitting areas ideal for entertaining. Dine waterfront for four or relax on four lounge chairs and Adirondack chairs around the outdoor fire pit.

Important Rental Details

Minimum Stay: 28 days

Check-in: 4 PM | Check-out: 10 AM (No early check-ins or late check-outs to ensure thorough cleaning and sanitation)

Occupancy Restrictions:

Up to 8 guests include use of the 1st floor only.

For 9-12 guests, the 4th bedroom (Bonus Room) is included for an additional charge.

No baggage holding or extra bedding/supplies provided to reduce cross-contamination.

Enhanced cleaning protocols are strictly enforced for guest safety.

Come Castaway on Sugarloaf Key—your peaceful sanctuary surrounded by nature’s beauty and endless water adventures. We look forward to hosting you!
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 28
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)
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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, a first aid kit and a deadlock
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Summerland Key

Located in Summerland Key, this holiday home is in a rural area and on the waterfront. Coupon Bight Aquatic Preserve and Upper Sugarloaf Sound reflect the area's natural beauty and area attractions include Wilhelmina Harvey Park and Blue Hole. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting.
Map
Upper Sugarloaf Key, FL

What's nearby

  • Upper Sugarloaf Key - 5 min drive - 2.1 km
  • Florida Keys Beaches - 18 min drive - 12.3 km
  • Sugarloaf Beach - 19 min drive - 12.9 km
  • Boca Chica Nude Beach - 37 min drive - 26.4 km
  • Duval Street - 41 min drive - 39.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 28 min drive

Restaurants

  • ‪Morning Joint - ‬10 min drive
  • ‪Baby's Coffee - ‬11 min drive
  • ‪Broil - ‬8 min drive
  • ‪The Bent Prop - ‬8 min drive
  • ‪Mangrove Mama's - ‬5 min drive

Frequently asked questions

Is Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

What time is check-in at Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot?

Check-in begins at 4:00 PM.

What time is check-out at Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot?

Checkout is at 10:00 AM.

Where is Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot located?

Situated on the waterfront, this holiday home is 1.3 mi (2.1 km) from Upper Sugarloaf Sound and 1.3 mi (2.1 km) from Upper Sugarloaf Key. Lower Sugarloaf Sound and Venture Key are also within 6 miles (10 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 5 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 1 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.0/10

Listing accuracy

Reviews

8/10 Good

James T.

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

Castaway review winter 2024

We enjoyed our stay. Fantastic views and porches. Great kitchen and dining amenities. Second bathroom was inconvenient to shower due to being inside whirlpool bath.
Stayed 37 nights in Mar 2024

10/10 Excellent

Todd W.

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

Group Trip

Great location. Lots of wildlife. Excellent layout for our group of 11. Kitchen was well stocked. Boat lift was easy. Would go back in the future.
Stayed 30 nights in Jun 2023

10/10 Excellent

Harley K.

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

It was so nice we decided to rent it next year

We have been fortunate to have rented many properties and this is one of our favorite. A great review is one in which the renters like it so much they rent it again which we did. Great location view, Upper unit layout of house is very comfortable. The lower unit does need to be updated.
Stayed 42 nights in Jan 2024

10/10 Excellent

Kevin K.

Stayed 28 nights in Jul 2025

6/10 Okay

Ralph H.

Liked: Cleanliness, check-in, communication, location

Over priced

house needs updating
Stayed 33 nights in Jan 2023

10/10 Excellent

Theresa E.

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

Great Views, Clean & Comfortable Home

We had a great stay at Castaway. With 8 guests, 1 dog and boat. The home is very comfortable and clean and has a fantastic family sleeping accommodation on 1st floor which makes it a great home for travelers with two families. The hot tub was a great was to spend the morning & evenings enjoying the waterfront views. The boat lift was also nice as it allowed us to not have to launch and haul out the boat every day and kept it clean while we stayed for the month. The master bedroom has a new deck off the side and the home is well outfitted for all guests needs. Will definitely return.
Stayed 7 nights in Oct 2021

10/10 Excellent

Theresa E.

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

Absolutely Perfect!

The home is perfect for multiple / split families with its upstairs/downstairs configuration. The area is very quiet and neighbors are friendly. It’s close to a school where kids can run an play in the fields after hours. The boat lift was great for our bay boat and the waterfront home is well kept and maintained. Would definitely stay here again and recommend it for others who want to be out of the hustle and bustle of Key West.
Stayed 5 nights in Oct 2021

About the host

Hosted by Conch Collection

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests