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Experience the Original Key West Houseboat — Now Docked on Stock Island

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A boat deck with two striped lounge chairs, a steering wheel, and a view of a calm water body with distant land.
A cabin with a wooden interior, large windows, a captain's wheel, and a sofa.
A cabin with a wooden control panel, a sofa, and large windows offering a view of the water.
A compact kitchen with wooden cabinets, a refrigerator, stove, and a sink.
A room with a bed, a wooden dresser, a chair, and a window overlooking a body of water.

Reviews

9.0 out of 10
Wonderful

Entire house boat

1 bedroom1 bathroomSleeps 3

Popular amenities

  • Ocean view
  • Kitchen
  • Pet friendly
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪15 min walk‬
  • Place, Florida Keys Beaches
    ‪17 min walk‬
  • Place, Smathers Beach
    ‪20 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

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About the neighborhood

Key West

With a stay at this houseboat in Key West (New Town), you'll be within a 5-minute drive of Florida Keys Beaches and Smathers Beach. .This houseboat is 2.1 mi (3.4 km) from Duval Street and 2.9 mi (4.6 km) from Mallory Square.
View more Houseboats in Key WestOpens in a new window

What's nearby

  • Key West Naval Station - 15 min walk - 0.8 miles
  • Florida Keys Beaches - 17 min walk - 0.9 miles
  • Smathers Beach - 20 min walk - 1.1 miles
  • Regal Key West - 4 min drive - 1.1 miles
  • Clarence S. Higgs Memorial Beach Park - 6 min drive - 1.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 6 min drive

Restaurants

  • ‪Denny's - ‬17 min walk
  • ‪Circle K - ‬18 min walk
  • ‪Starbucks - ‬9 min walk
  • ‪Taco Bell - ‬10 min walk
  • ‪Tin Cup Chalice - ‬4 min drive

About this property

Experience the Original Key West Houseboat — Now Docked on Stock Island

Experience the Original Key West Houseboat — Now Docked on Stock Island!

Looking for a unique and unforgettable Florida Keys getaway? Step aboard the original Key West houseboat and experience island life from a whole new perspective! Hosted by a seventh-generation local, this one-of-a-kind stay combines the charm of living on the water with the convenience of being docked on beautiful Stock Island, just 6 miles from downtown Key West.

Whether you’re looking for a romantic getaway, an adventurous vacation, or a relaxing escape, this houseboat offers an experience you won’t find at an ordinary hotel.

🌴 An Authentic Florida Keys Experience

This isn’t your typical vacation rental. This is a real houseboat with plenty of character, local history, and the laid-back atmosphere that makes the Florida Keys so special.

The houseboat is now conveniently docked on Stock Island, where you’ll be surrounded by the authentic working-waterfront atmosphere that makes this part of the Keys so unique.

Even better, you’ll be located between two fantastic waterfront restaurants!

* Hogfish Bar & Grill — A famous local favorite known for its fresh seafood, laid-back atmosphere, and authentic island character.
* The Docks Restaurant + Raw Bar — Another fantastic waterfront dining destination where you can enjoy delicious food and soak up the Florida Keys vibe.

You’ll be able to enjoy these local favorites without having to travel far from your floating home!

🛥️ Stay Dockside or Take Your Adventure Offshore!

One of the best things about this experience is the flexibility to make your vacation your own.

Enjoy the convenience of a dockside stay, with no need to operate a skiff or boat just to get to shore. You’ll have easy access to land, nearby restaurants, and all the adventures the Florida Keys have to offer.

Want something a little more adventurous?

For an additional fee, you can inquire about having the houseboat anchored in a secluded location away from the hustle and bustle, offering a more private and adventurous experience surrounded by the beautiful waters of the Florida Keys.

Imagine waking up surrounded by nature, enjoying your morning coffee on the deck, watching the sunset over the water, or spending the evening under a sky full of stars.

Secluded anchoring is an optional experience subject to availability, weather, and location.

🏡 Comfort and Character on the Water

The houseboat offers the comforts you need to relax and enjoy your stay, including:

* Full-size refrigerator and freezer
* Microwave and stovetop
* Hot water and a full-size shower
* Comfortable queen-size Sleep Number bed
* Solar power and generator
* Spacious upper deck for sunsets and stargazing
* A unique waterfront setting with beautiful views

Whether you’re enjoying breakfast on the deck, relaxing after a day of exploring, or watching the sky change colors at sunset, the houseboat gives you a memorable place to call home during your stay.

🚲 Explore the Florida Keys

Stock Island is a great starting point for exploring everything the area has to offer.

Head into downtown Key West to experience the famous Duval Street, visit the Ernest Hemingway Home and Museum, explore historic Old Town, or catch one of Key West’s legendary sunsets.

Golf carts and scooters can be delivered to the Houseboat

Spend your days snorkeling, fishing, kayaking, exploring the local marinas, or enjoying fresh seafood at nearby restaurants.

You can experience the excitement of Key West while returning to a more relaxed waterfront setting at the end of the day.

Whether you choose the convenience of staying dockside on Stock Island or inquire about an optional secluded anchoring experience, this is your opportunity to enjoy the Florida Keys in a way that goes beyond the ordinary.

Come for the adventure. Stay for the sunsets. Leave with memories that last a lifetime.

Book your stay and experience the original Key West houseboat for yourself!

⚓ Want to Get Out on the Water?

As a seventh-generation local and 50-ton Master Captain, I’m happy to share my knowledge of the area and help guests discover some of the best experiences the Florida Keys have to offer.

Looking for an unforgettable day on the water?

Ask about these additional experiences:

* 🤿 Snorkeling trips: Explore the beautiful waters and marine life of the Florida Keys.
* 🏝️ Sandbar excursions: Spend time relaxing in the shallow, turquoise waters at local sandbars.
* 🌇 Sunset cruises: Experience a beautiful Florida Keys sunset from the water.

Please note: Snorkeling trips, sandbar excursions, and sunset cruises are separate experiences and are not included in the houseboat’s nightly rental rate. These activities must be arranged separately and are subject to availability, weather, and additional fees.

🎣 World-Class Fishing Right Around the Corner!

Stock Island is a fantastic destination for fishing enthusiasts, with mini fishing charters conveniently located nearby, offering both nearshore and offshore fishing adventures. Whether you’re looking to catch snapper and other local favorites in the shallows or head offshore in search of bigger game fish, there are options for anglers of all experience levels.

With the beautiful waters of the Florida Keys right at your doorstep, it’s easy to turn your houseboat getaway into a fishing adventure you’ll never forget! Ask about nearby charter options during your stay and experience some of the incredible fishing that makes the Florida Keys famous.

🎬 A Houseboat with a Little Music History

This houseboat even caught the attention of country music band Old Dominion, who used it to film their music video for “I Was on a Boat That Day”!

Now it’s your turn to experience the charm of this unique floating getaway.

Whether you choose the convenience of staying dockside on Stock Island or arrange an optional secluded anchoring experience, you’ll have the opportunity to enjoy the Florida Keys in a way that goes beyond the ordinary.

🌴 Your Florida Keys Adventure Starts Here

Come experience the original Key West houseboat and discover why life on the water is something special.

Enjoy nearby waterfront restaurants, explore the excitement of downtown Key West, relax on the deck, or upgrade your stay with an optional secluded anchoring experience.

Come for the adventure. Stay for the sunsets. Leave with memories that last a lifetime.
There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach loungers

Internet

  • Available in the accommodation: Internet access

Parking and transportation

  • Wheelchair-accessible parking available

Kitchen

  • Coffee/tea maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Bedrooms

  • 1 bedroom

Bathroom

  • 1 bathroom
  • Hair dryer
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • One pet total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 on-site accessible parking spaces
  • No elevator
  • Wheelchair-accessible parking
  • Smoking not allowed

Things to do

  • Kayak

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

Policies

Check-in

Check-in time starts at 3:30 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

$100 for each additional guest after two

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
1 total pets

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

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
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators

Experience the Original Key West Houseboat — Now Docked on Stock Island Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 18 out of 22 reviews
Rating 8 - Good. 0 out of 22 reviews
Rating 6 - Okay. 1 out of 22 reviews
Rating 4 - Poor. 2 out of 22 reviews
Rating 2 - Terrible. 1 out of 22 reviews

9.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great boat, and great place to fish for sharks and snapper , brought our own boat to tie off and got to explore lots of the keys. Unique experience and love the camping style right on the water.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Different experience

We enjoyed the time there
Stayed 2 nights in Aug 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommended for quiet time

This was one of our best stays ever! This boat is not fancy but served us well. Key West is busy and full of people, we had our own little piece of paradise for 2 nights. Fished right off the boat, had a little skiff of our own to go back and forth and Vaughn treated us well. We would love to come back someday! Thank you:)
Stayed 2 nights in Feb 2024
Verified review

2/10 Terrible

Disliked: Cleanliness, check-in, communication, location, listing accuracy
Totally misinterpreted the house boat - it was not at a dock as we thought but moored out through a channel and only accessible by a skiff every time you needed to get off or on - absolutely impossible situation for my husband waiting for knee surgery using a brace and walking stick - notified owner and vrbo we could not do this - even drove to owners location in a very sketchy neighborhood - we were shocked. mislead and disappointed - we deserve at least a partial refund or may never use vrbo again and you better review your rentals better - Gretel Taylor 603 387 0605
Stayed 2 nights in Jan 2026
Verified review

4/10 Poor

Liked: Cleanliness, check-in, communication, listing accuracy

Not for us

We are good with camping but we struggled. 1. It’s very hot in August and we were not able to be comfortable without AC running 2. We were not able to get the toilet to flush #2. 3. We were surprised by how far the boat was from the shore. Because of this, we never kayaked back to shore. 4. Bring plenty of water and food with you as you don’t want to have to bring more in.
Stayed 3 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely Wonderful

We had the best time aboard the houseboat. It was a unique way to experience the keys. The owner was super helpful and a seven generation native of the keys. He made sure we were taken care of for our whole stay. We even had some kayaks and were able to see a manatee while kayaking in the canals. Great experience. Thanks for sharing your boat with us!!
Stayed 2 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect relaxing getaway

I can’t say enough about this great vacation experience! So relaxing under the stars but only 5 min to key West’. We loved watching the fish and even saw a dolphin swimming around the boat in the morning while we watched the Sunrise! We are repeat guests, just can’t say enough about this great vacation getaway in the Keys
Stayed 3 nights in Mar 2022
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities
Best Birthday for my hubby in quiet environment ❤️☀️👣 Our host Vaughn did an excellent job! No regrets we defy book again near the future
Stayed 2 nights in Mar 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great escape to Key West

This was our second time renting, it is nothing short of fabulous. This has turned out to be our secret place to escape and unwind. The host is very nice and very knowledgeable about the area and things to do, it’s a different and great way to experience the Keys. 5 min to Duvall street and everything you need. Just love it
Stayed 3 nights in Mar 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quick island getaway

What a cute floating love shack!! Owner was super helpful and attentive. All questions were answered immediately and was super friendly. Super great for star gazing and super private! literally 5min from shore and Key West. Already planning gnext stay
Stayed 4 nights in Nov 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

The most unique vacation I’ve ever had.

I’m not even sure where to start. Everything about this rental is as unique and genuine of an experience you can get. Vaughn was an exceptional host and just a nice genuine person. This is a Boat. I repeat this is a boat. I will say this stay is not for everyone but if you love the water, Have a little boating experience and like to experience life outside of cookie cutter experiences there is no better option in key west. The boat was super clean and perfect for a couple. The sunsets are magnificent and the skiff ride to and from the boat was one of my favorite parts. I cannot comment on the AC as we never even turned it on. We Just opened all of the windows and there was tons of breeze which made for perfect sleep. In response to some of the previous reviews that mentioned some issues. I can honestly say that those are exaggerated unless you have unreal expectations about what staying on a boat is about. Seriously I cannot say enough good things about this stay we WILL be back.
Stayed 4 nights in Nov 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay On The Water!

My husband and I stayed on the houseboat for 4 nights and loved every minute of it! Other than the grocery store, we didn't leave the boats for the first 2 1/2 days. The views are unparalleled! The water is crystal clear and the sunsets are some of the most spectacular we have ever seen! It was the epitome of relaxing!! There is a skiff you need to take back and forth to land and the trip through the mangroves is mesmerizing. With that being said, we are also avid boaters and felt completely comfortable using the skiff to get in and out. Vaughn is very knowledgeable about everything Key West related, having been born and raised there. Great guy! We cannot wait to come back and stay on the boat again! Thanks for a fantastic vacation!
Stayed 4 nights in Nov 2021
Verified review

6/10 Okay

Liked: Cleanliness, communication, location

Camping on the water

If your looking for a camping on the water experience, this is it. This is not for relaxation due to the location of the boat. It’s a 10 minute ride from where you park your car, through a canal and to the boat. Due to this inconvenience, you can’t enjoy the night life down town of key west. You will have to go before night fall because it is Pitch black going throw the canal to get back to the boat. Once on board, the window AC unit is meant just for sleeping which you have to mount your self. The unit is very Noisy at night in addition to the generator. Bring Non-perishable food, because even though they have a refrigerator, it will not stay on all day, unless the Generator is on which the owner told us to shut off everything when leaving for the day. There is no stove but a gas grill and no where to eat. Again, this is not for relaxing this is meant for camping on the water.the owner was very nice, he did explain everything. I was expecting another experience, I didn’t enjoy key west at it full potential due to having to leave before night fall.
Stayed 2 nights in Oct 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Staying on Happy's Houseboat

My wife and I chose a 2 week house boat vacation as another adventure to celebrate our 40th year together. We understood the limitations of these accommodations and accepted the challenge. As a result, we had one of the best vacations to date and plan to do it again in the future. Vaughn Willis did his best to make our stay enjoyable and was patient with all our questions. We expect the best from our host and he met that expectation.
Stayed 13 nights in Oct 2021
Verified review

4/10 Poor

Liked: Cleanliness
Disliked: Communication, listing accuracy

So many hopes

We had so many hopes for this trip. It didn’t live to our expectations. 1. Communications were unpredictable and often problematic. At times the owner responded within hours just to disappear for days, apologize and disappear again. It became especially problematic after we departed. I forgot my wallet at the property. Notified the owner from the airport; he responded fast, stated that he would overnight the wallet, just to disappear yet again. The item has not been returned after 2 weeks. No communication from owner with any updates. Notified VRBO. 2. I maybe wrong, but I think I overpaid for this rental. Summer nights are hot in Key West. Night breeze doesn’t cut it. The air conditioning is useless as it only works in one place. That had been mentioned in the listing. What wasn’t mentioned- musty smell in that room. If you have allergies or asthma- beware. 3. No one’s fault, but low tides are really low. To the point that you can’t jump off the boat. And that was a major reason to rent one. 4. Kayaks are not available. 5. Stairs to get to the water are absent. You have to improvise to get on and off. 6. Toilet - I do not recommend to use it for #2. Go to the shore and find a bathroom. 7. We won’t be back.
Stayed 3 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Awesome!
Stayed 3 nights in May 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Host

Our honeymoon was made perfect by this stay and our going above and beyond host!
Stayed 7 nights in Oct 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet time getaway!

Great place with no people around. It's an RV on the water, nothing fancy but worth the view. Vaughn was great and took care of us well!
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Getaway

From the moment we met Vaughn at the skiff and took a beautiful trip through the mangroves to the boat we were hooked. This was a true getaway while at Key West. The views from the boat were a perfect way to rejuvenate. The boat was as advertised and we thoroughly loved this experience. You have the freedom to come and go as you please with the skiff. Vaughn was happy to help/answer questions and took great care of us. Not a better way to enjoy Key West!
Stayed 4 nights in Mar 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

We had a great time. Was so nice to get out of the chaos of the city and have some peace and quiet.

Great time.
Stayed 3 nights in Feb 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unforgettable experience!!!

My husband and I celebrated our 30th anniversary on this boat, and it was one of the most memorable experiences we have ever had!! The water was crystal clear, the sunsets were glorious and the boat was spacious and comfortable. It was a fun filled camping experience on the water. Amazing location in the middle of the bay, very private with great views on every side. We will definitely come back for this one of a kind adventure. Vaughn was a super nice host and we had good communication with him before the trip and during our stay. Looking forward to our return!
Stayed 3 nights in Jan 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Jan 2025