Living the Dream Key West Style

Key West, Florida
$428 avg/night
Minimum Stay 1 Nights
Bed 3

Bed

Bath 3

Bath

Home House Boat

Property Type

Sleep 6

Max Sleeps

Night 1 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Service Animals Only (pets Not Allowed)
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Property Does Not Allow Children
  • KITCHEN

    Ice Maker Oven Refrigerator Stovetop
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Patio
  • POOL/SPA

    Hot Tub
  • BATHROOMS

    3 Bathrooms
  • THINGS TO DO

    Kayak On Site Paddleboard On Site
  • ENTERTAINMENT

    Stereo Smart TV
  • CLIMATE CONTROL

    Air Conditioning
  • SUITABILITY/ACCESSIBILITY

    No Elevators Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Kathy A

    Submitted Mar 1, 2026

    Stayed Feb 16, 2026

    everything was perfect

  • Mikael

    Submitted Jan 22, 2026

    Stayed Jan 17, 2026

    Perfect, just perfect!

  • Debra

    Submitted Nov 15, 2025

    Stayed Nov 6, 2025

    Everything was very nice. Staff was friendly and helpful .

  • Alison

    Submitted Oct 27, 2025

    Stayed Oct 25, 2025

    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!

  • Todd

    Submitted Oct 25, 2025

    Stayed Oct 23, 2025

    Clean rooms pet friendly great view! Exactly as advertised

  • Marco

    Submitted Feb 8, 2025

    Stayed Feb 6, 2025

    Wonderful spot, great hosts. Spectacular sunset cruise aboard Serenity.

  • Lucinda

    Submitted Feb 23, 2024

    Stayed Feb 22, 2024

    Great hosts. Went out for fantastic sunset cruise. Very friendly. Interior of the Serenity was clean and size was good. Everything went well.

  • Jennifer

    Submitted Feb 18, 2024

    Stayed Feb 16, 2024

    The boat was beautiful, clean and spacious. Our hosts were amazing and went out of their way to make it a very memorable experience! There was a great restaurant/bar within walking distance. Will definitely stay here again!!

  • Josh C.

    Submitted Apr 19, 2026

    Stayed Apr 18, 2026

    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.

  • Taylor S.

    Submitted Apr 9, 2026

    Stayed Apr 8, 2026

    It was a super nice and really neat older boat that gives you that live aboard charm.

  • Laura Hunt L.

    Submitted Apr 8, 2026

    Stayed Mar 15, 2026

    Dear Abby and Glenn, aka Santa’s Key West sailing elves—Thank you for two glorious days aboard Serenity. Your genuine hospitality, kindness, and warm welcome made our stay truly special. The sunset sail tonight was incredible, and sharing such a beautiful evening with you was a highlight of our time in Key West.By decree of the North Pole, Santa has named you honorary members of the Worldwide Remote Workers League of Elves for spreading cheer, kindness, and true Christmas spirit wherever you sail.You are hereby recognized by your official elf titles: Glenston Frost Mariner Abbyshore TidesongThank you for being such wonderful hosts.With gratitude and Christmas cheer,Laura & Greg

  • Carol Z.

    Submitted Apr 6, 2026

    Stayed Apr 2, 2026

    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!

  • Michael W.

    Submitted Mar 31, 2026

    Stayed Mar 27, 2026

    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!

  • carol g.

    Submitted Mar 30, 2026

    Stayed Mar 13, 2026

    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!

  • Zach C.

    Submitted Mar 27, 2026

    Stayed Mar 25, 2026

    Great would definitely stay again

  • Jacquelyn S.

    Submitted Mar 25, 2026

    Stayed Mar 18, 2026

    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.

  • Cheryl S.

    Submitted Mar 2, 2026

    Stayed Feb 26, 2026

    Glenn and Abby were fantastic host. Their hospitality was above any other host we have ever stayed with.

  • Jeff P.

    Submitted Feb 17, 2026

    Stayed Feb 12, 2026

    Great boat. Sunset cruise was great. Only downside was it wasn’t in the best neighborhood.

  • Elizabeth D.

    Submitted Feb 16, 2026

    Stayed Feb 15, 2026

    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!

  • Steven T.

    Submitted Feb 16, 2026

    Stayed Feb 14, 2026

    Everything with the stay was perfect. Glen was a fantastic host. The accommodations were better than we could have imagined. Location was convenient to everything Key West has to offer. It was a unique experience and we will be returning when we can stay longer.

  • William G.

    Submitted Feb 11, 2026

    Stayed Feb 4, 2026

    Everything was wonderful. Glen and Abby were super friendly and welcoming. The boat was very comfortable and we enjoyed the marina area.

  • Eric S.

    Submitted Feb 8, 2026

    Stayed Feb 7, 2026

    Host was great, Experiece was awesome, would definitely recommend to anyone.

  • Alex B.

    Submitted Feb 4, 2026

    Stayed Jan 31, 2026

    The stay was great! The host was extremely friendly and helpful. We will be back!

  • J C.

    Submitted Jan 26, 2026

    Stayed Jan 24, 2026

    Very welcoming! Neat, clean! Only wosh we could have stayed longer!!! Would definitely go back!

  • Jeff B.

    Submitted Jan 20, 2026

    Stayed Jan 14, 2026

    Wonderful boat for a very unique day. The host was there for support but not intrusive. Five stars.

  • natalie e.

    Submitted Jan 2, 2026

    Stayed Dec 31, 2025

    Everything was perfect. Communication, location, the boat itself. And the host hot tub was a great bonus. Super relaxing trip!

  • George C.

    Submitted Dec 31, 2025

    Stayed Dec 28, 2025

    Everything is as described on the listing. Glen is super friendly and very attentive. Boat is clean and spacious. Only downside is we didn't get to spend enough time there.

  • Tom M.

    Submitted Dec 12, 2025

    Stayed Nov 29, 2025

    All around great time. Glen and Abby couldnt be better

  • Ben T.

    Submitted Dec 9, 2025

    Stayed Nov 24, 2025

    It’s hard to pick out one thing, but everything was great and Glen and Abby were awesome. They did everything to make sure we felt welcomed and comfortable during our stay. Being our first time in Key West, they had all the local knowledge of things to do and where to go. They answered any/all questions we had. The sunset cruise was awesome and we got some interesting history about the local area and some of the other boats. We went during Thanksgiving and they invited us to enjoy their feast even though we weren’t expecting it and they didn’t have to. It turned out to be a perfect relaxing and quiet vacation and we would definitely stay here again.

  • J&R F.

    Submitted Nov 19, 2025

    Stayed Nov 15, 2025

    Glenn was super welcoming and a cool dude. Very accommodating. Great location and beautiful marina. Hope to check it out again!

  • Jeff P.

    Submitted Nov 17, 2025

    Stayed Nov 1, 2025

    Clean and unique place to stay for the night. The owner was extremely helpful. Met us at the gate and helped with all of our needs.I highly recommend this as a different experience from a house or a condo in Key West. You won't regret it.The next time we will reserve an excursion and take the boat out for a sail.

  • Jim M.

    Submitted Oct 29, 2025

    Stayed Oct 12, 2025

    Whar a unique stay, had never stayed on a boat before. Would highly recommend. Sailboat was in emaculate condition. Glen and his wife were super friendly, awesome folks!

  • Emily D.

    Submitted Oct 20, 2025

    Stayed Oct 18, 2025

    Such a special stay and the hosts were incredibly helpful and friendly! Went above and beyond to make our stay nice.

  • Mariel M.

    Submitted Oct 12, 2025

    Stayed Oct 10, 2025

    Great hosts and great time. Friendly and very helpful. Highly recommend this listing. We can’t sit to come back

  • Lyndon M.

    Submitted Oct 7, 2025

    Stayed Sep 29, 2025

    The hosts were welcoming and provided great recommendations on things to do in Key West. They advertised pet-friendly and they were very accommodating. The highlight of the trip was the sunset cruise that was customized to really give us great views of Key West and the sunset. Captain Abbie and Glen even let us stear the the boat around. Absolutely incredible experience.

  • Jodi M.

    Submitted Sep 28, 2025

    Stayed Sep 26, 2025

    Everything was excellent, awesome host, beautiful vacation!

  • Steve F.

    Submitted Sep 25, 2025

    Stayed Sep 18, 2025

    The hosts were exceptional.

  • Kandice T.

    Submitted Sep 16, 2025

    Stayed Sep 5, 2025

    Amazing stay! The getaway my husband and I truly needed and enjoyed. Peaceful and truly serene! Glen and sidekick Charlie were attentive, friendly and knowledgeable and we will absolutely be back! Most likely with friends and family. Would 10/10 recommend!

  • Richard D.

    Submitted Sep 2, 2025

    Stayed Aug 30, 2025

    The drive up to the boat is through a very rough neighborhood that had us a little uneasy. Once you get through the gate it is nicer leading up to the boat. The property manager lives right next to the boat so he is quick to help with any questions. Upon entering the vessel we noticed a strong odor in the galley area that smelled like the black water tank but not sure. The kitchen ware is very dated and for the price of the stay I expected to be nicer. Please be aware this boat moves ALOT for its size even in calm waters. If you get even slightly sea sick I would not recommend staying as you will not be refunded anything even if you spend only 10 mins on the boat.

  • Henriett K.

    Submitted Aug 1, 2025

    Stayed Jul 27, 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.

    Submitted Jun 30, 2025

    Stayed Jun 19, 2025

    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.

  • Nancy M.

    Submitted Apr 18, 2025

    Stayed Apr 4, 2025

    Great hosts and great accommodations!

  • Mary O.

    Submitted Mar 18, 2025

    Stayed Feb 28, 2025

    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.

  • Joseph L.

    Submitted Feb 17, 2025

    Stayed Feb 14, 2025

    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!

  • Janet B.

    Submitted Feb 16, 2025

    Stayed Feb 11, 2025

    We had a wonderful stay. Enjoyed staying at the marina. Sitting out in the evenings. Perfect weather. Walked to a local restaurant that was great. Thanks for being a wonderful host.

  • Valerie R.

    Submitted Feb 3, 2025

    Stayed Jan 25, 2025

    We had a wonderful and fun experience staying 2 nights on Serenity. The hosts were great communicators and always available if needed. Definitely would recommend!

  • Sandi W.

    Submitted Dec 1, 2024

    Stayed Nov 28, 2024

    The Serenity is a beautiful boat! My kids loved mixing it up and doing something different. I wish we had more time to enjoy the boat and the harbor. Everything was clean and comfortable. Glen and Abby were so kind and friendly. It’s about 15 min to get to the main marina and downtown Key West, even if the map says 4 miles. I’d love to come back and have Abby take us on a sail!

  • April R.

    Submitted Nov 29, 2024

    Stayed Nov 25, 2024

    We had an awesome stay and Glen was the perfect host. Very personable and great to talk to. I would stay there again.

  • Leslie O.

    Submitted Nov 13, 2024

    Stayed Nov 8, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$532+
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