Living the Dream Key West Style
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1 night
1 room, 2 adults, 0 children
All properties in Stock Island

Living the Dream Key West Style

Boat
Stock Island, Florida, 33040
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Highlights
Excellent service
Sparkling clean
Ideal location
Amenities
Kayaking
BBQ
No smoking in public areas
All amenities
Property Description
Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large world cruising sailboat on the sailing vessel Serenity. Staying on Serenity is what Key west is known for and living a carefree lifestyle. Experience and enjoy the Artistic and Tropical landscaped private marina with spectacular views of the harbor. Lounge in the hammock and watch the sunset or sit on the dock and grill out watching the shrimp boats come and go. This is a all inclusive price. No cleaning fee and includes 2- paddle boards and 4- Kayaks Serenity is docked at Safe Harbour Marina which is a beautiful tropical landscape marina in Stock Island which is a 15-minute ride to downtown Key West. There is the Famous locals Restaurant and Bar the Hogfish located at the Marina. Serenity is on the point of the marina and has nice views with a large dock with outside seating. Safe Harbour is a very secure marina and has a small friendly community of liveaboards that look out for everybody. Our cohost Glen lives in the cottage in front of Serenity and are available to address any issues that occur and share his local knowledge of the Island and values your privacy and will not disturb you. There is plenty of seating in front of Serenity on the dock that is exclusively for Serenity guests only with a nice sitting area with a grill to enjoy the beautiful sunset Key West is famous for. There are two refrigerators and an ice maker. There are all cooking utensils on board you might need. One private parking spot provided in a locked gated driveway. Serenity is a 1983 60 ft Catalina /Morgan Schooner. It has the classic beautiful teak interior that the older sailing vessels are known for. A large, covered cockpit to sit and enjoy sunsets. There is one large stateroom with a Queen-size bed and its own private bathroom. There are two separate smaller staterooms with a twin bed that can be pulled out to a full in each. There is an additional single bunk in the captains' quarters off the galley. The galley has a propane stove and oven, large kitchen sink, large drawer refrigerator, a large icemaker and plenty of storage. The saloon is large with plenty of seating and a large table that can folds in half to give more space. There is a tv for your entertainment and free starlink wifi. A Fusion stereo system with Bluetooth to enjoy your favorite playlists. Serenity just had a major refit with all new systems In it, Interior and exterior wood all newly refinished and exterior newly painted, all new appliances, new cushions throughout the boat and is maintained on a regular basis. Per USCG we are required to have a bareboat agreement on board and will send a copy to your email address provided to us and will need it to be signed 24 hours before your check in time. We offer the following excursions and encourage you to book one which will be one of the best moments of your stay. This is above Vbro costs and will need to be booked separately within 24 hrs of your booking through Vbro. These excursions will provide you with a memorable experience. Serenity sails beautifully and you can learn the art and thrill of sailing. You will be allowed to steer the boat help put out the sails if you wish or just sit back and relax while the crew does all the work. 2-hour sunset sail. $600.00 plus tax and a gratuity to your captain. 6 -hour sail to the Reef for snorkeling with lunch provided. $1,200.00 plus tax and a gratuity to your captain. 24 - hour overnight at anchor with a license captain on board $2,000.00 plus tax Charters and Rentals subject to availability and weather. Hurricane Season. Please note Serenity is a large sailboat and per insurance regulations and the safety of the boat, the boat will be hauled out of the water if there is a threat of a named storm developing with key west in its path. This will make the boat unavailable for a period of 10 days or more. Per Vbro rules we as hosts our not allowed to cancel a reservation without severe penalty's unless it falls within their guidelines which a threat of a named storm is not considered into it becomes a named storm. We will inform you the boat will be hauled out due to a threat of a named storm and you will need to cancel the reservations which we will give back a full refund which you will need to request with your cancellation Serenity has beautiful wood floors and large suitcases with wheels tend to scratch the floors. In order to keep Serenity looking good we only allow soft sided luggage such as backpacks, garment bags and duffle bags. If you are not traveling by car, we can store your large luggage in the owner's cottage next to Serenity. We have complimentary tote bags to transfer your belongings onboard. Serenity is docked stern to, boarding the boat involves walking across a boarding ramp that we call the gangway and descending stairs into the cabin that we call the companionway. It is always safest to maintain three points of contact with the ship while boarding and moving about the deck and the cabin.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:Bareboat Charter agreement to be signed 24 hrs before check in through Adobe E Sign. Can not let you board Serenity without a digitally signed copy..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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10.0/10
Outstanding
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 18 reviews
Surroundings
Airport: Key West International Airport
(5.3 km)
Landmarks: Try Scuba Diving - Key West
(<100m)
Landmarks: Up The Keys Tours
(<100m)
Landmarks: El Mar RV Resort
(290m)
Landmarks: Stock Island Marina Village
(330m)
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Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

Three-Bedroom Houseboat
4

Three-Bedroom Houseboat

Non-smoking
Room Details
Check Availability

Guest Reviews

10.0/10
Outstanding
18 reviews
Verified Reviews
  • Cleanliness10.0
  • Amenities10.0
  • Location10.0
  • Service10.0
Average for similar properties in Stock Island
Most Mentioned
G‍u‍e‍s‍t‍ ‍U‍s‍e‍r
August 1, 2025
Great experience! It was my first time staying on a boat and it was amazing. The hosts were very nice and helpful, the boat was very clean and welcoming.
C‍h‍r‍i‍s‍t‍o‍p‍h‍e‍r‍ ‍I‍.
June 30, 2025
Amazing Glen & Abby are wonderful people. They went above and beyond to accommodate my wife and I. We are grateful that they allowed us to get married on Serenity, it was absolutely perfect. If you're looking for something different this is it....it's a completely different vibe than your typical hotel or VRBO rental. And I highly recommend having them take you out on the sunset cruise it's worth every penny and you won't regret it. Thanks again Glenn & Abby it was a weekend we'll never forget.
L‍e‍s‍l‍i‍e‍ ‍O‍.
November 13, 2024
So much fun! There was 5 of us and there was plenty of room. It was clean and the owners were very on top of things with great communication.
M‍a‍r‍y‍ ‍O‍.
March 18, 2025
Darlene Absolutely wonderful!! Our hosts went really out of their way to make our stay perfect. When we checked out, I felt like I was leaving my new best friends.
V‍i‍p‍i‍n‍ ‍G‍.
December 2, 2023
2 days of FUN Glen provided a wholesome experience during our night yacht stay in Key West. The beautiful and well-equipped yacht, along with a sunset sail, fun activities like snorkeling and kayaking, and even a water slide, made our stay memorable. Glen's role as a perfect host and personal lifeguard added an extra layer of comfort. Highly recommend this fantastic getaway!"
K‍a‍t‍h‍r‍y‍n‍ ‍M‍.
February 29, 2024
Amazing! Boat is beautiful! Abby and Glen were amazing hosts. I would highly recommend booking a sunset tour with them. It won’t disappoint! Cabin is comfortable and clean. Nothing like being rocked to sleep on the water. This was a great stay, and I would highly recommend!!
L‍u‍c‍i‍n‍d‍a
February 24, 2024
Great hosts. Went out for fantastic sunset cruise. Very friendly. Interior of the Serenity was clean and size was good. Everything went well.
J‍o‍s‍e‍p‍h‍ ‍L‍.
February 17, 2025
Wish we stayed longer! My wife and I stayed on the Serenity and found it to be exactly what we were looking for! Glen was a most gracious and amiable host and made us feel welcomed and at home. Our visit was cut short due to poor planning, but to wake up on that boat with the waves gently rocking you to sleep at night and the quiet marina, certainly made one understand why the boat is aptly named Serenity, Will plan to make another stay to last longer but this was an experience that was everything we hoped it would be!
J‍e‍s‍s‍e‍ ‍L‍.
January 26, 2024
Boat life Key West style! We had an amazing stay! Serenity was absolutely beautiful, incredibly roomy and comfortable, and our hosts were more than accommodating! Walking distance to Hogfish Bar & Grille, only minutes to downtown, it was a truly unique to Key West experience. Highly recommend staying here! We can’t wait for our next visit and will definitely stay here again if it’s available!

Services & Amenities

More Amenities
Health & Wellness
Public Areas

Property Policies

Check-in and Check-out Times
Check-in: After 15:00
Check-out: Before 11:00
Child Policies
Children are not permitted to stay in this room type.

Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.

Age Requirements
The main guest checking in must be at least 18 years old

Property host

About this property

Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large world cruising sailboat on the sailing vessel Serenity. Staying on Serenity is what Key west is known for and living a carefree lifestyle. Experience and enjoy the Artistic and Tropical landscaped private marina with spectacular views of the harbor. Lounge in the hammock and watch the sunset or sit on the dock and grill out watching the shrimp boats come and go. This is a all inclusive price. No cleaning fee and includes 2- paddle boards and 4- Kayaks Serenity is docked at Safe Harbour Marina which is a beautiful tropical landscape marina in Stock Island which is a 15-minute ride to downtown Key West. There is the Famous locals Restaurant and Bar the Hogfish located at the Marina. Serenity is on the point of the marina and has nice views with a large dock with outside seating. Safe Harbour is a very secure marina and has a small friendly community of liveaboards that look out for everybody. Our cohost Glen lives in the cottage in front of Serenity and are available to address any issues that occur and share his local knowledge of the Island and values your privacy and will not disturb you. There is plenty of seating in front of Serenity on the dock that is exclusively for Serenity guests only with a nice sitting area with a grill to enjoy the beautiful sunset Key West is famous for. There are two refrigerators and an ice maker. There are all cooking utensils on board you might need. One private parking spot provided in a locked gated driveway. Serenity is a 1983 60 ft Catalina /Morgan Schooner. It has the classic beautiful teak interior that the older sailing vessels are known for. A large, covered cockpit to sit and enjoy sunsets. There is one large stateroom with a Queen-size bed and its own private bathroom. There are two separate smaller staterooms with a twin bed that can be pulled out to a full in each. There is an additional single bunk in the captains' quarters off the galley. The galley has a propane stove and oven, large kitchen sink, large drawer refrigerator, a large icemaker and plenty of storage. The saloon is large with plenty of seating and a large table that can folds in half to give more space. There is a tv for your entertainment and free starlink wifi. A Fusion stereo system with Bluetooth to enjoy your favorite playlists. Serenity just had a major refit with all new systems In it, Interior and exterior wood all newly refinished and exterior newly painted, all new appliances, new cushions throughout the boat and is maintained on a regular basis. Per USCG we are required to have a bareboat agreement on board and will send a copy to your email address provided to us and will need it to be signed 24 hours before your check in time. We offer the following excursions and encourage you to book one which will be one of the best moments of your stay. This is above Vbro costs and will need to be booked separately within 24 hrs of your booking through Vbro. These excursions will provide you with a memorable experience. Serenity sails beautifully and you can learn the art and thrill of sailing. You will be allowed to steer the boat help put out the sails if you wish or just sit back and relax while the crew does all the work. 2-hour sunset sail. $600.00 plus tax and a gratuity to your captain. 6 -hour sail to the Reef for snorkeling with lunch provided. $1,200.00 plus tax and a gratuity to your captain. 24 - hour overnight at anchor with a license captain on board $2,000.00 plus tax Charters and Rentals subject to availability and weather. Hurricane Season. Please note Serenity is a large sailboat and per insurance regulations and the safety of the boat, the boat will be hauled out of the water if there is a threat of a named storm developing with key west in its path. This will make the boat unavailable for a period of 10 days or more. Per Vbro rules we as hosts our not allowed to cancel a reservation without severe penalty's unless it falls within their guidelines which a threat of a named storm is not considered into it becomes a named storm. We will inform you the boat will be hauled out due to a threat of a named storm and you will need to cancel the reservations which we will give back a full refund which you will need to request with your cancellation Serenity has beautiful wood floors and large suitcases with wheels tend to scratch the floors. In order to keep Serenity looking good we only allow soft sided luggage such as backpacks, garment bags and duffle bags. If you are not traveling by car, we can store your large luggage in the owner's cottage next to Serenity. We have complimentary tote bags to transfer your belongings onboard. Serenity is docked stern to, boarding the boat involves walking across a boarding ramp that we call the gangway and descending stairs into the cabin that we call the companionway. It is always safest to maintain three points of contact with the ship while boarding and moving about the deck and the cabin.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:Bareboat Charter agreement to be signed 24 hrs before check in through Adobe E Sign. Can not let you board Serenity without a digitally signed copy..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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Frequently Asked Questions

What is the cancellation policy for Living the Dream Key West Style?

The cancellation policy for Living the Dream Key West Style varies depending on the type of room and booking conditions.

What are the check-in and check-out times at Living the Dream Key West Style?

Standard check-in time at Living the Dream Key West Style is 15:00 and check-out time is 11:00.

How far is the Living the Dream Key West Style from the closest airport?

The closest airport is Key West International Airport, and it is about 11 mins from hotel by car (5.3 km).

About This Property

Nearest AirportKey West International Airport
Distance to Airport5.31KM
Hotel Star Rating3