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 by Vrbo and will need it to be signed 24 hours before your check in time. As this is a boat we our required to go over safety equipment and make sure you're comfortable with handling any emergency situations so we cannot offer self-check ins and have to meet you on the boat on your check in. Because of this we cannot do late check ins without prior written ok which is subject to our availability. Our last check in is 6:00 pm.
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 and guests, 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 Vrbo 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 until 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 if you wish not to cancel your reservation and we our forced to honor the reservation the boat will be made available to stay on in the boat yard. Please note there will be no Air Conditioning and you will have to climb a 16 ft ladder to board Serenity. The boat will be highly uncomfortable.
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.
Our prices include all fees. No hidden fees.
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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.
No late check ins (After 6:00pm) without written approval
Important information
You need to know
Property # 3672438
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
About the neighborhood
Key West
Key West is home to this houseboat. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Smathers Beach. Key West Tropical Forest and Botanical Garden and Sails To Rails Museum at Flagler Station are also worth visiting.
Stock Island Yacht Club & Marina - 3 min drive - 1.7 km
Key West Tropical Forest and Botanical Garden - 3 min drive - 2.0 km
Getting around
Key West Intl. Airport (EYW) - 10 min drive
Restaurants
Hogfish Bar & Grill - 1 min walk
Hurricane Hole Marina - 4 min drive
Bad Boy Taqueria & Tequila - 3 min drive
Toasted Coconut - 5 min drive
El Siboney Stock Island - 13 min walk
Frequently asked questions
Is Living the Dream Key West Style pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at Living the Dream Key West Style?
As of May 10, 2026, prices found for a 1-night stay for 2 adults at Living the Dream Key West Style on May 11, 2026 start from $404, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Living the Dream Key West Style?
Check-in begins at 3:00 PM.
What time is check-out at Living the Dream Key West Style?
Check-out is at 11:00 AM.
Where is Living the Dream Key West Style located?
Situated in Key West, this houseboat is within 2 mi (3 km) of Stock Island Yacht Club & Marina, Robbie's, and Key West Tropical Forest and Botanical Garden. Florida Keys Community College Library and Clark Maxwell Environmental Habitat are also within 2 mi (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Everything was great with the rooms, the nail in the coffin for a great Key West trip. Property Managers were helpful and knowledgeable about everything, from the ship itself to the surrounding area. The sunset cruise was so relaxing and worth every bit of the cost. The whole group loved it and will definitely be looking forward to going back.
Fantastic experience! Glen and Abby were the absolute perfect onsite hosts and ensured our stay was perfect. The Serenity was a beautiful boat, with comfortable accommodations and completely unique way to enjoy Key West. Thanks for the beautiful sunset cruise - it was a great way to end our stay!
From the moment we met Host Glen, we had smiles on our faces! Check in communication was perfection, the sailboat was amazing and a super fun experience! We can't wait to come back! I would give six stars if I could!
Abby and Glen were great. They answered any questions we needed greeted us when we arrived to make sure we had a tour on the sailboat helping us find are way around. Thank you Abby and Glen.
Beautiful boat with great amenities. The hosts were very kind and welcoming. I was a solo traveler and felt very safe the entire time. I would love to come back eventually! Thank you so much for having me!
Our last night on the Keys, our group of 6 stayed on the Serenity. It was a WOW for sure! The ship itself was beautiful and only outmatched by the hospitality. From booking w/ Nicholas to our host and captain, Glen, what a perfect adventure! Glen & Abby took us on a sunset cruise where we captured beautiful sunset pictures of our group that are now in frames in our homes. We made amazing memories on this boat to last a lifetime.I highly recommend staying on the Serenity and taking the sunset cruise!
Liked: Cleanliness, amenities, property conditions & facilities, communication
We thoroughly enjoyed our stay on Serenity! The location was perfect, the hosts were friendly and accommodating, and the boat is spacious and comfortable. I hope to be back aboard Serenity soon!
Alison
Stayed 1 night in Oct 2025
Verified
10/10 Excellent
Todd
Oct 25, 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
Clean rooms pet friendly great view! Exactly as advertised
Todd
Stayed 2 nights in Oct 2025
About the host
Hosted by Nicholas
Premier Host
They consistently provide great experiences for their guests