Happy’s Houseboat Key West

Key West, Florida
$581 avg/night Minimum Stay 2 Nights
Bed 1

Bed

Bath 1

Bath

Home House Boat

Property Type

Sleep 3

Max Sleeps

Night 2 nights

Min Stay

This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on a boat that day”, it has a sleep number bed, hot water and full-size fridge. The Boat is nestled in a very calm bay protected from waves. The beautiful sites surround you as you wake up on the water and the sunsets and stars give you great experiences as you relax on the top deck in the evening. Included in the rental is use of a 13 foot motor boat to get to and from the houseboat.

You have 360° ocean views sunsets sunrises stargazing. You can jump right off the boat into the golf of Mexico. Rental of the houseboat includes use of a 13 foot skiff to get yourself to and from land as well as plenty of parking.

Boating experience is required as you will be out on the water and get yourself to and from the boat. It is important that you are aware that this is a houseboat. Your electric is coming to the form of solar or generator power. There is a water heater and For size shower. There’s also a fridge and microwave. The bed is a sleep number which is adjustable on either side of the bed. There is AC in the bedroom. However the rest of the boat is called with the Ocean breeze in box fans. The top deck is beautiful place to watch sunsets or gaze at the stars. An extra cleaning fee will be charged if dishes are left in the sink or the house is left in very unclean conditions.


This is the best place to stay in The Fl Keys great location beautiful views and an amazing experience, hosted by a six generation local. This is on a houseboat so basic knowledge of the water is recommended. You will have to get yourself to and from the houseboat on a 13 foot skiff. I’ll meet you to check you in and show you the way out to the boat as well as how everything on the boat works like the generator and solar power. The boat does have a full-size fridge, microwave oven, stove top, hot water full size shower, sleep number queen size bed, top deck for sunsets and star gazing , everything you’ll need to be more that comfortable.

I am a six generation local to Key West. And also a licensed captain. I will be available during your stay to take you out to secluded islands in sandbars for snorkeling dolphin watching light tackle fishing or to just relax and enjoy the beautiful scenery. If you are interested in booking one of these charters during your stay I will be available weather permitting

Plenty of free safe parking is available at the check-in location where the dock is that you will use to get to and from the houseboat. That being said there is not a captain on this boat and I will not be there to assist you with everything so it is important that you can start a generator and the motor on the boat to get you to and from the house boat. They are in perfect working condition however this can be an issue for some people.

This is a houseboat in the Caribbean. It can get hot. you will be using a generator and solar for power. If you check into this house boat and then realize that it is not a hotel room you will not be refunded. This is similar to camping however on a boat that has the amenities however you will have to use a generator and solar for any electrical needs.

This boat is not for complainers nor land lovers. This is a boat I repeat this is a boat.

Check in

I will meet you at the check-in location at a time we scheduled prior to your arrival to show you where to park in the Skiff you will use to get to and from the houseboat. You’ll then follow me out to the houseboat so I can show you have everything on the houseboat works. I’m available if you need assistance during your stay. But everything is very simple to use as long as you do have basic knowledge and our somewhat familiar with the water.

Guest access

The entire boat is yours and your nearest neighbors are far away in the bay. So you’ll feel very private and secluded as you enjoy this unique experience. Access to and from the boat is made to use of a 13 foot kayak provided with the use of the rental. As well as one ride in when you check in and out. Water taxi is available however it is a very short kayak trip.

Other things to note

There is a full-size fridge. There is AC in the bed room however the rest of the boat is cooled with the ocean breeze. Most people don’t use the AC as the breeze and a fan make it very comfortable. However this is a boat in the Caribbean so on some days it can be hot. The toilet is a little different than yours at home main difference being that you won’t put toilet paper down the head it will go into a trashcan. An extra cleaning fee will be charged if dishes are left in the sink or the house is left in very unclean conditions. If you plan to do a lot of barhopping or partying on Duval this may not be the place for you either although you can get to and from land very easily and quickly this boat is special because it offers the other side of Key West like peaceful calm ocean views sunsets snorkeling.

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

Feature Features

  • PETS

    1 Total Pets Pet Friendly
  • BEACH

    Beach Sun Loungers
  • 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

    1 Bedroom
  • KITCHEN

    Coffee/tea Maker Microwave Oven Refrigerator Stovetop
  • PARKING

    Onsite Parking Wheelchair-accessible Parking Available
  • INTERNET

    Internet Access
  • OUTDOORS

    Barbecue Grill Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Hair Dryer Toilet Paper Towels Provided
  • THINGS TO DO

    Kayak On Site
  • ENTERTAINMENT

    Smart TV
  • CLIMATE CONTROL

    Air Conditioning
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Wheelchair-accessible Parking

CheckIn Check-in : 03:30 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 3

Map Map

School District Rates & Availability

Review Review

  • Leland

    Submitted Mar 24, 2022

    Stayed Mar 21, 2022

    Best Birthday for my hubby in quiet environment ❤️☀️? Our host Vaughn did an excellent job! No regrets we defy book again near the future

  • Submitted May 21, 2021

    Stayed May 17, 2021

    Awesome!

  • Judy T.

    Submitted Jan 25, 2026

    Stayed Jan 23, 2026

    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

  • Morgan G.

    Submitted Oct 5, 2025

    Stayed Oct 3, 2025

    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.

  • Jodi E.

    Submitted Mar 3, 2024

    Stayed Feb 27, 2024

    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:)

  • Kristy T.

    Submitted Aug 16, 2022

    Stayed Aug 12, 2022

    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.

  • Stacy W.

    Submitted May 24, 2022

    Stayed May 19, 2022

    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!!

  • cynthia s.

    Submitted Apr 3, 2022

    Stayed Mar 30, 2022

    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

  • cynthia s.

    Submitted Mar 6, 2022

    Stayed Mar 2, 2022

    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

  • cynthia s.

    Submitted Nov 28, 2021

    Stayed Nov 24, 2021

    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

  • Jay S.

    Submitted Nov 22, 2021

    Stayed Nov 17, 2021

    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.

  • Bianca D.

    Submitted Nov 17, 2021

    Stayed Nov 12, 2021

    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!

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Total

Includes taxes and fees
$581+
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