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Day trips and overnight trips are available with our captainor just cruise around key west
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Straycat Sailing Entire Boat

Chester & Charlie User Profile
Chester & Charlie

Straycat Sailing Entire Boat

8 guests
4 bedrooms
4 beds
2 baths
8 guests
4 bedrooms
4 beds
2 baths
Great check-in experience
100% of recent guests gave this home’s check-in process a 5-star rating.

Stay on our 4 bedroom sailboat and you’ll have a vacation you won’t believe including a nightly 2 hour sunset sail with our captain.
This spacious vacation rental on the water comfortably sleeps up to 8 guests and is completely air-conditioned and heated to keep you comfortable. Our full kitchen makes meal preparation a snap with a refrigerator, microwave convection oven and cooktop. All linens and towels are included in the rental.


Free parking on premises
Cable TV
Air Conditioning

House Rules

Check-in is anytime after 3PM and check out by 11AM


45 Reviews

Stephen User Profile
October 2018
I'm still feeling incredible when I think of it , which was such strange and interesting experience.
Gisselle User Profile
June 2018
Charlie was an AMAZING Host. We rented a one night stay to celebrate my husband’s 30th birthday with a group of friends, and it was absolutely perfect. Charlie made it so much more unique and unforgettable. We did a sunset sail and went for a quick dip, so much fun! Can’t wait to…
Cristina User Profile
May 2018
There was a lot of wind the day we went, so the sailing wasn’t that great, but at least we got to do it, sometimes it’s not possible to go out because of the rain. The boat doesn’t have a double bed in the living room as the description says. We got out of water in the tank and t…
Kathy User Profile
May 2018
We had a great time on the Stray Cat! A unique stay for our family and a trip that will be talked about for years to come.
Caitlin User Profile
April 2018
We had an amazing stay on the StrayCat with Captain Charlie- the expirence was unique, the bedrooms were perfectly clean with soft sheets and nice mattresses! Sunset sails and swims were incredible- Overall a unique and wonderful stay!
Ginger User Profile
March 2018
A great experience. We loved the evening sails! If you want a luxury hotel this isn’t for you, but if you want something a little different with a local vibe this is a fun option. We had plenty of room for 2 adults and three teens. The “living room” on the dock was a nice touch …
Charles User Profile
January 2018
Awesome day charter sailing.

Hosted by Chester & Charlie

Key West, Florida, United StatesJoined in February 2015
Chester & Charlie User Profile
855 Reviews
It has been my dream to sail and live on the water. I spent 10 years in south Texas doing dolphin watches, dinner cruises, sailing charters and overnight sailing excursions. I relocated to Key West several years ago and became an Airbnb host. I love taking guests snorkeling, lob…
Languages: English
Response rate: 100%
Response time: within an hour
Always communicate through AirbnbTo protect your payment, never transfer money or communicate outside of the Airbnb website or app.

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