Title: Key West Sailing Adventure - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire house boat # Key West Sailing Adventure Bayside houseboat in Key West with beach bars ## Photo gallery for Key West Sailing Adventure ![Exterior detail - Key West Sailing Adventure (Key West)](https://images.trvl-media.com/lodging/2000000/1560000/1555200/1555152/e75ee734.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Wild Thing 44' Sailboat includes 2-hour Sunset Cruise | Living area - Key West Sailing Adventure (Key West)](https://images.trvl-media.com/lodging/2000000/1560000/1555200/1555152/1a5e92bf.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Food court - Key West Sailing Adventure (Key West)](https://images.trvl-media.com/lodging/2000000/1560000/1555200/1555152/90948061.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Wild Thing 44' Sailboat includes 2-hour Sunset Cruise | Living area - Key West Sailing Adventure (Key West)](https://images.trvl-media.com/lodging/2000000/1560000/1555200/1555152/80ca8e99.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Wild Thing 44' Sailboat includes 2-hour Sunset Cruise | Private kitchen - Key West Sailing Adventure (Key West)](https://images.trvl-media.com/lodging/2000000/1560000/1555200/1555152/85f6e5a0.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Rooms - Location - Policies A short walk from Mallory Square and Duval Street, Key West Sailing Adventure provides 2 beach bars, an art gallery on site, and a shopping mall on site. Adventurous travelers may like the sailing at this houseboat. Free in-room WiFi and laundry facilities are available to all guests. ## Reviews 7.0 Good ## Popular amenities - Free WiFi - Air conditioning - Parking available - Bar - Laundry - Kitchen ## Room options ### Check availability for these dates Tonight [Dec. 26 - Dec. 27](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Dec. 27 - Dec. 28](https://www.expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Dec. 26 - Dec. 28](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-28&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-28&selected=1555152&PinnedHotelID=1555152&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Jan. 2 - 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[Sign in](https://www.expedia.ca/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Hotels-Key-West-Sailing-Adventure-With-Sunset-Charter-Included.h1555152.Hotel-Information)[Sign up, it's free](https://www.expedia.ca/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Hotels-Key-West-Sailing-Adventure-With-Sunset-Charter-Included.h1555152.Hotel-Information) ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.56108%2C-81.80103&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=SG3i4hNsVxmZgvgfZvd2QWH1ckk=) 201 Williams Street; Historic Seaport, E-Dock Slips E-10, E-11, E-12, Key West, FL, 33041 #### What's nearby - Key West Historic Seaport \- 1 min walk \- 0.0 km - Florida Keys Beaches \- 6 min walk \- 0.5 km - Duval Street \- 6 min walk \- 0.6 km - Mallory Square \- 9 min walk \- 0.8 km - Harry S. Truman Little White House \- 11 min walk \- 0.9 km #### Getting around - Key West Intl. Airport (EYW) - 14 min drive #### Restaurants - ‪Kermit's Key West Key Lime Shoppe - ‬3 min walk - ‪Conch Republic Seafood Company - ‬6 min walk - ‪Cuban Coffee Queen Waterfront - ‬2 min walk - ‪Schooner Wharf Bar - ‬1 min walk - ‪Half Shell Raw Bar - ‬3 min walk ## About this property ### Key West Sailing Adventure Houseboat near Duval Street Close to Mallory Square and Ernest Hemingway Home and Museum, Key West Sailing Adventure provides 2 beach bars, an art gallery on site, and a shopping mall on site. Active travelers can enjoy sailing at this houseboat. Free in-room WiFi and laundry facilities are available to all guests. Additional perks include: - Outdoor pool access nearby - Self parking (surcharge) and smoke-free premises Room features All guestrooms are individually furnished, and feature comforts such as air conditioning, as well as thoughtful touches like free WiFi and free bottled water. More conveniences in all rooms include: - Showers and free toiletries - Kitchens, refrigerators, and microwaves ## Similar properties ![House, Multiple Beds (3 4 Tim e) | Living room](https://images.trvl-media.com/lodging/60000000/59660000/59659300/59659271/e3d8fd90.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 3 4 Tim e Northside Resort - Pool - Parking included - Gym - Outdoor Space [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&selected=59659271&PinnedHotelID=59659271&HadPinnedHotel=true®ionId=-1&adults=2) ![House, Multiple Beds (Southern Comfort) | Interior](https://images.trvl-media.com/lodging/60000000/59660000/59659300/59659289/9d723753.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Southern Comfor t Northside Resort - Pool - Parking included - Gym - Outdoor Space [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&selected=59659289&PinnedHotelID=59659289&HadPinnedHotel=true®ionId=-1&adults=2) ![House, Multiple Beds (Seafarer's Refuge) | Pool](https://images.trvl-media.com/lodging/60000000/59640000/59639400/59639306/1a98b3c7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Seafarer's Refuge Key West Historic District - Pool - Parking included - Outdoor Space - Babysitting [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&selected=59639306&PinnedHotelID=59639306&HadPinnedHotel=true®ionId=-1&adults=2) ![Condo, Multiple Beds (Middle Sunset) | Lake](https://images.trvl-media.com/lodging/60000000/59660000/59659400/59659318/1ed5e750.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Middle Sunset Meadows - Pool - Parking included - Spa - Gym [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&selected=59659318&PinnedHotelID=59659318&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### NYAH Key West - Adults Only Key West Historic District - Pool - Hot tub - Breakfast included - Air conditioning 8.0 Very good 1,000 reviews CA $294 CA $392 total includes taxes & fees Jan 21 - Jan 22, 2026 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-21&endDate=2026-01-22&selected=7500588&PinnedHotelID=7500588&HadPinnedHotel=true®ionId=-1&adults=2) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island - Pool - Pet friendly - Free WiFi - Restaurant 9.4 Exceptional 1,174 reviews CA $366 CA $495 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12&selected=17313680&PinnedHotelID=17313680&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in start time: 3 PM; Check-in end time: 6:00 PM Minimum check-in age: 21 ### Check-out Check-out before 11 AM ### Special check-in instructions There is no front desk at this property Guests will receive key retrieval information To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation If you are planning to arrive after 6:30 PM please contact the property in advance using the information on the booking confirmation For any questions, please contact the property using the information on the booking confirmation Information provided by the property may be translated using automated translation tools ### Access methods Key retrieval ### Pets Pets not allowed (service animals welcome) ### Children and extra beds Children are welcome Rollaway/extra beds are not available Cribs (infant beds) are not available ### Property payment types ## Important information ### Fees You'll be asked to pay the following charges at the property. Fees may include applicable taxes: - Cleaning fees vary based on length of stay We have included all charges provided to us by the property. ### Optional extras - Self parking fee: USD 30.00 per day The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change. ### You need to know 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 Minimum Spring Break check-in age is 21 years old This property accepts credit cards Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property ### We should mention This property does not have elevators Only registered guests are allowed in the guestrooms Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation ### Property is also known as Key West Sailing Adventures Boat Key West Sailing Adventure Private Sailing Charters House Boat Key West Sailing Adventure Sunset Charter Included Houseboat Sailing Adventure Private Sailing Charters Sailing Adventure Sunset Charter Included Houseboat Key West Sailing Adventure Sunset Charter Included Sailing Adventure Sunset Charter Included Sailing Adventure Sunset Char Key West Sailing Adventure With Sunset Charter Included Key West ## Frequently asked questions ### Does Key West Sailing Adventure have a pool? ### Is Key West Sailing Adventure pet-friendly? ### How much is parking? ### What time is check-in at Key West Sailing Adventure? ### What time is check-out at Key West Sailing Adventure? ### Where is Key West Sailing Adventure located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Reviews ## Key West Sailing Adventure Reviews 7.0 ### Good All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 6.6 Cleanliness ### 7.6 Location ### 6.8 Staff & service ### 6.6 Property conditions & facilities 10 - Excellent 5 8 - Good 2 6 - Okay 3 4 - Poor 0 2 - Terrible 3 ## Reviews ### 6/10 Okay #### SANDRA Feb 18, 2016 Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Uncomfortable accomodations-nice boat trip Reviews indicate poor conditions and they were true. While the owners of the boat were nice they did not have a good system for assuring that new employees were oriented or that the heat and lights were turned on. Not worth the daily price for the lodging, ##### SANDRA ### 8/10 Good #### Terry Mar 29, 2019 Liked: Cleanliness, staff & service, property conditions & facilities #### Key West alternative We enjoyed our stay on the sailboat as an alternative to staying in a hotel. However, this would not be suitable for everyone. Quarters are clean but somewhat cramped. Location is GREAT! Close to everything. Sunset cruise was wonderful. Captain Ben and crew are excellent! Only problem we had was getting on and off the boat. Needs a gangplank with hand holds. ##### Terry Stayed 3 nights in Mar 2019 ### 10/10 Excellent #### Sandra Jan 20, 2019 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### True Key West Adventure What an amazing way to spend New Year's Eve. The boat was so much fun to stay on. We were right in the harbor where all the fun was happening. The owners are really great and easy to work with. They called us and gave us all the info we needed plus their numbers to be contacted at. Our sunset sail was changed to a daytime sail which was much better for us. If you are looking for a fancy hotel this is not for you...its a boat. If you are looking to have a great Key West adventure the way the keys should be seen this is it!! Can't wait to go back. Thank you for an unforgettable holiday. ##### Sandra Stayed 2 nights in Dec 2018 ### 10/10 Excellent #### Thomas Jun 28, 2017 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Obsession Captain Al and his crew met and exceeded any need that we had. It was great staying on the sailboat and we had a wonder sailing adventure. ##### Thomas Stayed 3 nights in Jun 2017 ### 10/10 Excellent #### Glenn, Florida Sep 10, 2016 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Dream Come True I have always wondered if I could rent a sailboat and stay for a couple days and there it was. I often dream of owning my own sailboat so this would be that experience It was easy to find. I already knew where to go. Checking in went fast and easy. We were shown everything about staying aboard and then some. We were given a key and shown us the "facilities" which had a restroom and shower if we required. Or you could use the boats. He spoke to us of several restaurants and things to do in Key West. We met the next morning for a sail, fishing and snorkel day of adventure. Our crew Knew their way around a sailboat and the Key West waterway. We had a tremendous day. At night, we walked the piers/docks and made quite a few new friends with the folks living on their vessels. All had the same thoughts. "You only live once, just do it" Mr. Albert was always available. We spoke with him on the dock and told him what a wonderful experience this was for both me and my grandson. He runs a great business. He has a great crew. They have a lot of knowledge of the local area and of sailing/snorkeling and live aboard lifestyle. I would rate our experience a 10 if I could! ##### Glenn ### 6/10 Okay #### Don, Jupiter Fl Sep 29, 2013 Liked: Staff & service #### Cool place to stay You need to be a camper if you like this idea. We rode down on Motercycles and had a blast. Parking was a little tough but it was worth it to be so close to Duval. Slept 4 no problem but showers on board a little to small for my 6'2" frame so we used the marina showers. Capt Albert the owner was very eazy to reach and very accommodating. ##### Don ### 10/10 Excellent #### Chris, Altanta, GA Aug 3, 2013 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Can't get closer to the water !! We stayed on the 37 foot Obsession and it was perfect for two people. Albert and Susan were great; very helpful and had many recommendations for things to do and places to go and see. Also had a great sunset sail with Capt. Brian. Great birthday weekend for my wife!! ##### Chris ### 2/10 Terrible #### Clay, Atlanta GA May 3, 2011 Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Absolutely THE last place on earth We booked a 2 day stay and we were supposed to sleep on the Sailboat being used for our cruise. We arrived only to find a phone number on the dock post. We called and the person answered and said he was at sea but had left the boat open for us. We quickly discovered that there was a fuel leak on board and that the cabin was so toxic it made you immediatly sick to be in there. The instructions left behind in the toxic cabin told you not to use the bathrooms on the boat but in the public bathhouse, except that they forgot to leave a key to the bathhouse and thus we were locked out of the bathhouse and thus no bathroom, we called and we were told he would not return until 2p the next day. The city was sold out that weekend and we had to sleep on the top of the toxic boat, and that would have been fine except for the fact that it was 90 degrees in the shade and it was located in a slip in a busy harbor with hundreds of people and boats filing in and out of the harbor kind of sadly peering out at us sleeping on top of the toxic boat. ##### Clay ### 2/10 Terrible #### Crankie, St George, UT Nov 17, 2009 Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Unsanitary, repulsive and very dirty conditions I was most bothered that we paid a premier price for staying in a place without indoor plumbing. The restroom was unusable because we had to pump out the urine and pump in water every time we used the tiny toilet. The kitchen was filthy. The draws were full of junk left by previous visitors. There were zero amenities: no water, no soap, and no flush toilets. It was expensive camping; a premier price for an outhouse, middle of the night walks to the drunk-haunted public restroom one block away, and a miserable experience. Basically, we rented a dirty kitchen and very smelly and unusable restrooms in the middle of busy pier filled with drunken people and loud music throughout the night. ##### Crankie ### 2/10 Terrible #### Katherine, Huntsville Nov 2, 2009 Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Tired and Worn I was very disappointed with the sailboat Obsession. It has not been kept up and was tired and worn. To their credit, the sheets and two towels they provided were clean and in good condition and the air conditioner worked. The 4 hour sail and snorkeling included being towed back to the dock because the engine wouldn't start. If you are true sailors with high standards, this is not the boat for you! ##### Katherine ### 6/10 Okay #### David and Allison Apr 23, 2009 #### A unique experiance The boat is positivily relaxing...however, you only have the sounds of the bay and a radio. Not for the more pampered lifesttyles because you are far from that. I.E. no shower or tv. But the sails are beatiful and there is always something going on throughout the day in the marina. The crew was absolutly polite and we are thankful that they made our experiance very pleasant. ##### David and Allison ### 10/10 Excellent #### Verified traveller Dec 3, 2019 Liked: Cleanliness, staff & service, amenities, property conditions & facilities ##### Verified traveller Stayed 2 nights in Nov 2019 ### 8/10 Good #### Verified traveller May 1, 2009 ##### Verified traveller ## Expedia's Latest Trends ### Hotels > [Best Western Hibiscus Motel](https://www.expedia.ca/Key-West-Hotels-Best-Western-Hibiscus-Motel.h13680.Hotel-Information) > > [Courtyard by Marriott Key West Waterfront](https://www.expedia.ca/Key-West-Hotels-Courtyard-By-Marriott-Key-West-Waterfront.h663132.Hotel-Information) > > [Winslow's Bungalows - Key West Historic Inns](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) > > [The Reach Key West, Curio Collection by Hilton](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) > > [Fort Lauderdale Marriott Harbor Beach Resort & Spa](https://www.expedia.ca/Fort-Lauderdale-Hotels-Fort-Lauderdale-Marriott-Harbor-Beach-Resort-Spa.h21880.Hotel-Information) > > [Universal's Endless Summer Resort - Dockside Inn and Suites](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) > > [Universal's Endless Summer Resort - Surfside Inn and Suites](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Resort-Surfside-Inn-And-Suites.h27522522.Hotel-Information) > > [Fontainebleau Miami Beach](https://www.expedia.ca/Miami-Hotels-Fontainebleau-Miami-Beach.h1190549.Hotel-Information) > > [Parrot Key Hotel & Villas](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) > > [Fairfield Inn and Suites by Marriott Key West](https://www.expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.Hotel-Information) > > [Universal's Cabana Bay Beach Resort](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) > > [Beach House Fort Lauderdale, a Hilton Resort](https://www.expedia.ca/Fort-Lauderdale-Hotels-Hilton-Fort-Lauderdale-Beach-Resort.h28591.Hotel-Information) > > [Sunset Key Cottages](https://www.expedia.ca/Key-West-Hotels-Sunset-Key-Cottages.h17456804.Hotel-Information) > > [Loews Miami Beach Hotel – South Beach](https://www.expedia.ca/Miami-Hotels-Loews-Miami-Beach-Hotel-South-Beach.h81223.Hotel-Information) > > [Blue Flamingo Resort Key West](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) > > [Ibis Bay Beach Resort](https://www.expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) > > [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) > > [Casa Marina Key West, Curio Collection by Hilton](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) > > [Margaritaville Hollywood Beach Resort](https://www.expedia.ca/Fort-Lauderdale-Hotels-Margaritaville-Hollywood-Beach-Resort.h10005147.Hotel-Information) > > [The Tides on Hollywood](https://www.expedia.ca/Fort-Lauderdale-Hotels-The-Tides-On-Hollywood.h44524455.Hotel-Information) > > [W South Beach](https://www.expedia.ca/Miami-Hotels-W-South-Beach.h11881.Hotel-Information) > > [Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort](https://www.expedia.ca/Orlando-Hotels-Four-Seasons-Resort-Orlando-At-WALT-DISNEY-WORLD-Resort.h7374428.Hotel-Information) > > [Havana Cabana at Key West ](https://www.expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) > > [Universal’s Loews Royal Pacific Resort](https://www.expedia.ca/Orlando-Hotels-Universals-Loews-Royal-Pacific-Resort.h856706.Hotel-Information) > > [1 Hotel South Beach](https://www.expedia.ca/Miami-Hotels-1-Hotel-South-Beach.h1790087.Hotel-Information) > > [Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) > > [Diplomat Beach Resort Hollywood, Curio Collection by Hilton](https://www.expedia.ca/Miami-Hotels-Diplomat-Beach-Resort-Hollywood.h857779.Hotel-Information)