Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
3 bedrooms2+ bathroomsSleeps 6
Popular amenities
Kitchen
Air-conditioning
Gym
Outdoor space
Parking available
Explore the area
Key West, FL
Key West Naval Station
Place, Key West Naval Station
3 min walk
Stock Island Yacht Club & Marina
Place, Stock Island Yacht Club & Marina
6 min walk
Key West Golf Club
Place, Key West Golf Club
2 min drive
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
8 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Double Bed
Bedroom 3
1 Double Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Toilet
Spaces
Deck or patio
Kitchen
Kitchenette
Dining area
About this property
All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6
Welcome aboard the The Thirsty Lady with 3 bedrooms and 3 baths, your own private Sailboat that also includes your Sailing Excursions for up to 6 people. If you were looking for a Unique, Memorable way to experience and enjoy Key West then THIS IS IT!! You stay in amazing 5 Star Marinas each night and Sail by day, all included. If you book 2 nights that includes a Sunset Sail your first night of arrival and 1 full day Reef Sail. Book 3 nights and receive 1 Sunset Sail and 2 Full day Reef Sails and so on. We book 2 nights minimum and 4 nights max.. We always do the Sunset Sail your first night of arrival and then a day Sail is included for each day.
**Please understand that even though 1 Sail is included for each day you book doesn't mean you have to use them all. We have found that guests who book 3 or 4 nights sometime forgo a Sail or 2 to have a free day to do what they wish. It is totally up to you whether or not you use all the Sails included and you can decide as you go when you arrive😊**
We have years under our belt offering these charters and have decided to join the VRBO family to extend our reach. We are here to cater to all your special needs to make sure your experience with us will land in your top favorite vacations EVER! We provide the Captain, Captain Pat, a USCG 100 Ton Master Captain.
The first night of arrival we take you on a Sunset Sail and that night you will be docked at a beautiful Upscale 5 Star Marina that boasts 6 pools, Restaurant & Bar, 24 hour pristine Bath House, and free shuttle all available for you use. There are bathrooms on the boat but you will want to use the Bath House for showering located just steps from the boat..
The 2nd day we take you on a full day Sail to the Reef where you can swim, snorkel and Just Relax! The 2nd night you will be docked at another Amazing Upscale Marina. All the marinas offer amazing amenities including pools, bars, restaurants, and free shuttles. If you stay a 3rd night we take you on another day sail the 3rd day and you will stay back at the 5 Star Marina you stayed the 1st night. We do offer free parking for your entire stay and if you are carless there are free shuttles available to you and we can help you with rides when available. We also provide all your water, ice, and sodas for the length of your stay along with all your life jackets, safety gear, fresh linens and towels and snorkeling equipment. You are responsible for your meals but there is a small kitchen aboard with a fridge, freezer, toaster, and a small stovetop/oven. There are plenty of Restaurant/ delivery options available to you as well. Most people just pick up light snacks and lunch items to make sandwiches for their Day Sails. There is also a dining table that seats up to 6 people. You are responsible for your own alcohol but we usually have a pretty well stocked bar you are always welcome to. You are welcome to anything you see in the cabin! If you would like me to remove the alcohol from the boat please let me know. This is your own PRIVATE SAILBOAT made available to you with your own Private Captain that is only there when you are going out Sailing. The rest of your time off the water the boat is all yours. Captain Pat will only be there when you need him. We are 100 percent on call when you are staying with us so we will always be available if you need us. This trip is perfect for couples, friend get togethers and amazing for families!! We have hosted them all and every summer we Captain the boat out to the Boy Scouts of America. Please understand this is a Sailboat so space is limited in the cabin and the rooms are small but there is cold A/C and extremely comfortable to sleep on. The Front bed is a Queen and the back bedrooms are double/fulls. The beds will sleep 2 comfortably but you better like each, lol..What we are offering is something so different from what everyone else is doing and we so look forward to hosting all of you!! Please message us with any questions!
Sample Itinerary:
Day of Arrival: Guests usually arrive between 1-4pm. We will greet you and show you around and get you acquainted with the area and boat. 4:30-6pmish is a Sunset Cruise (subject to change when Sunset times change) The first night you will be docked at a 5 Star Upscale Marina which has 6 pools, a Restaurant & Bar, 24 hour bath house, Gym, and a free Shuttle that will take you downtown and back.
***You have to arrive by 4pm the latest on your arrival day if you want to take advantage of the Sunset Cruise***
The 4pm cutoff time will change throughout the year as Sunset times change. The other half of the year is a 5pm cutoff time when we leave the dock for when the Sun sets later in the evening and so on.
Day 2: We meet you back at the boat around 9-10ish am (you let us know what works for you) and we Sail you out for a full day at The Reef where you can swim & snorkel. You dictate how long we stay out for but usually we get back to dock around 3 or 4, all up to you. The 2nd night we take you to another beautiful Marina in Key West. All the marinas have pools, restaurants, bars and free shuttles. Basically Sail by Day and then you are free to leave the boat and explore Key West by afternoon/night.
3rd day: If you chose the 3 night stay we take you on another Day Sail to a different part of the reef and the 3rd night you will be docked where you were the first night. So basically if you book 2 nights that includes 2 Sails and 3 nights you receive 3 Sails.
We also offer 4 night stays which would include an extra Sail.
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Events allowed: family gatherings and birthday parties
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Pets
No pets allowed
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Smoking
Smoking allowed: in designated areas
Important information
You need to know
Property # 2492182vb
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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 6
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
About the area
Key West
Located in Key West, this houseboat is on the waterfront. 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. Take the opportunity to explore the area for water adventures such as power boating.
Stock Island Yacht Club & Marina - 6 min walk - 0.6 km
Key West Golf Club - 2 min drive - 2.0 km
Duval Street - 16 min drive - 9.6 km
Mallory Square - 19 min drive - 10.6 km
Getting around
Key West, FL (EYW-Key West Intl.) - 8 min drive
Restaurants
Hogfish Bar & Grill - 3 min drive
Hurricane Hole Marina - 5 min drive
Bad Boy Taqueria & Tequila - 4 min drive
El Siboney Stock Island - 3 min drive
Hurricane Hole Waterfront Bar & Grill - 5 min drive
Frequently asked questions
Is All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6 pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6?
As of 10 May, 2026, prices found for a 1-night stay for 2 adults at All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6 on 22 Oct, 2026 start from S$1,807, 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 at All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6?
On-site parking is available at the property.
What time is check-in at All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6?
Check-in begins at 4:00 PM.
What time is check-out at All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6?
Checkout is at 11:00 AM.
Where is All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6 located?
Situated on the waterfront, this houseboat is within 2 miles (3 km) of Stock Island Yacht Club & Marina, Key West Tropical Forest and Botanical Garden and Key West Golf Club. Robbie's and Florida Keys Community College Library are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This was an amazing trip, as first timers in the Florida Keys, Captain Pat was incredibly patient and gave us the insider scoop on places to go and things to try. We had the most amazing sailing days with snorkeling. Both marinas were lovely - if you are reading this review to try and see if you should book the trip - DO IT! An amazing host, lovely sailboat, and the perfect experience!
We had a wonderful time on the Thirsty Lady. Great way to unwind in a relaxed setting and still be close to all the fun in downtown Key West. Captain Pat, PJ and Stephanie were awesome to work with, and the sailing was great. Boat was very comfortable for us and the marine facilities were top notch with nice bath houses, restaurants, pools and shuttle services to Key West. We hope to book this vacation rental again!
Our trip to Key West aboard the Thirsty Lady was unforgettable. I traveled with my daughter and her boyfriend, and the three of us had plenty of room to relax and enjoy the beautiful sailboat. Captain Pat and his son PJ were fantastic hosts — friendly, knowledgeable, and incredibly helpful with local recommendations for food and things to do.On our first day, we enjoyed a peaceful sunset cruise before spending the night on the boat and taking in the Key West nightlife. The next morning, we headed out for a day sail to the reef, where we snorkeled in clear water and soaked up perfect sunny weather — warm but never too hot. Later that evening, we moved to a marina in downtown Key West, had a great dinner, and stayed on board again. The final day took us on another relaxing sail back to the original marina.Everything about the experience was excellent — the sailing, the snorkeling, the atmosphere, and especially the hospitality. We had an amazing time and will definitely be booking this adventure again.
Great way to meet some real boat captains and see the best of key west. Stay away from the tourist traps and book this stay with captain Pat and PJ. Staff was attentive and accommodating to all of our requests. Felt like I was sailing and snorkeling with some old friends. Super chil. Great way to get away. Don’t keep looking just book it.
My family and I had a wonderful stay and adventure on the Thirsty Lady. Pat, PJ, Stephanie, and Pat's wife were accommodating and bent over backward to ensure everything was perfect. They even went to the airport to pick us up and dropped us off at our hotel after our stay with them. They took us snorkeling and sailing for a day, and we stayed at two exceptional marinas with all the perks of a resort. The fun part was getting to know Pat and his son PJ while listening to their awesome life and sea stories. Pat also provided lots of good restaurants and sightseeing recommendations! I highly recommend booking with them and having a fantastic trip like we did. We will be back one day.
Such an amazing trip! Excellent communication from booking all the way to boarding the boat.
Captain Pat gave us recommendations for stops on our drive down through the Keys. Then he met us at the gate and showed us around the property before our sunset cruise. The boat was stocked with drinks for our trip. It comfortably slept 2 adults and 4 kids aged 10-17. We had two different day cruises to separate snorkeling locations. Our kids are all strong swimmers and had no problems with the open water snorkeling. It was great that Captain Pat and PJ let our family get in on the action while sailing. Our second night at Opal Key was steps away from Mallory Square and fantastic restaurants & bars. Captain Pat also gave us a variety of "must visit" places to check out.
For breakfast, we highly recommend "Two Friends" while docked at Opal Key and a quick drive to either "DeLuna's" or "El Mocho" while docked at Oceanside Marina.
We highly recommend booking this trip!!
My wife and I had a lovely 3 night stay on the Thirsty Lady. Capt Pat and his son PJ are great. They are very friendly and we felt as if we were part of their family. Capt Pat has extensive knowledge of Key West including bars and restaurants. If you are the type of person who seeks out authentic experiences and likes the idea of living on a boat, you will like his recommendations.
Life on the boat is a bit cramped, but comfy. There is a fridge, sink, and a cook stove (that we never used). The bathrooms are small and really just for essential use. The main Marina has very nice private bathrooms and showers.
There is not much nearby the Marina, but there is an hourly shuttle to the downtown area, or you can catch a ubiquitous Uber
The Marina for the second night is downtown. The amenities are not as nice, but the location is spectacular. You can watch the sunset from your boat and crash back into the boat after a late night of Duval street shenanigans.
Through no fault of theirs, we had a somewhat abbreviated sailing experience. Waves and wind made the snorkeling a bit of a challenge. The reef was very nice for an open water snorkel. Our third day was very windy and one of the stays snapped, cutting short our sail. Capt Pat offered to drive us around Key West and was extremely gracious
Throughout the trip Capt Pat and his family did everything to make sure we had a great stay. They are outstanding hosts!
Had a great time on the boat. It rained 1 day but we were able to make up the sailing time the next day. Captain Pat was great and we also really really appreciate his son PJ.
Our stay on the sailboat was amazing! Captain Pat and PJ took us on beautiful sails where we snorkeled and swam. Stephanie is the hostess with the mostest! This was one of her best vacations ever!
We were looking to do something different then staying at a resort. This was the perfect experience and exactly what we were looking for. Captain Pat, PJ and Stephanie were very accommodating.
Captain Pat and PJ and Stephanie were amazing! We thoroughly enjoyed our first stay on a sailboat and the communication was 10++++! Marinas were outstanding with pools and nice clean bathing facilities. The two included cruises out on the boat were stellar, my kids favorite part of the whole trip. Would def stay again!
Booking process - was a breeze! Stephanie answered all of my questions! She even personalized the boat with a welcome/Happy Birthday sign, balloons, and amazing cupcakes!
Sailing - it was pretty windy when we went but it was still so much fun! Captain Pat and PJ are awesome and so friendly! It was our first time sailing and they made sure we felt okay and had a great time!
The boat - The boat is super super cute!! It was clean and well stocked. They stocked the coolers with ice, water, pop, and some beers/wine! Each stateroom has its own bathroom!! Also, the beds are comfortable!
I would totally recommend this trip to anyone wanting to experience staying on a boat!!! We cannot wait to come back and visit!
Cassandra J.
Stayed 3 nights in Dec 2021
About the host
Hosted by Stephanie Clines
Languages:
English
Premier Host
They consistently provide great experiences for their guests