House boat

Living the Dream Key West Style

Photo gallery for Living the Dream Key West Style

A sailboat with a covered deck and a person relaxing in a hammock.
A sailboat docked at a marina with a clear sky and palm trees in the background.
A marina with boats docked, a wooden dock with a table and chairs, and an American flag.
A compact kitchenette with a sink, a Keurig coffee maker, and a refrigerator.
A compact kitchen with a coffee maker, a sink, and a wine rack.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Wake up on the waves
    A rare find — sleep on the water in this unique houseboat stay.
  • Discover nearby landmarks
    Near Key West Golf Club

Popular amenities

  • Hot tub on site
  • Patio
  • Outdoor grill
  • Air conditioning
  • Refrigerator
  • Onsite parking available

Explore the area

View in a map
Key West, FL
  • Place, Key West Golf Club
    ‪15 min walk‬
  • Place, Key West Naval Station
    ‪18 min walk‬
  • Place, Stock Island Yacht Club & Marina
    ‪3 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Kitchen

Add dates for prices

Similar properties

Pool
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Stock Island
  • Pool
  • Kitchen
  • Pet friendly
  • Air conditioning
10.0 out of 10, Exceptional, (7 reviews)
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

About the neighborhood

Key West

Key West is home to this houseboat. 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar.
View more Houseboats in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Key West Golf Club - 15 min walk - 1.3 km
  • Key West Naval Station - 18 min walk - 1.6 km
  • Key West Tropical Forest and Botanical Garden - 3 min drive - 3.1 km
  • Stock Island Yacht Club & Marina - 3 min drive - 2.4 km
  • Duval Street - 17 min drive - 9.3 km

Getting around

  • Key West Intl. Airport (EYW) - 10 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Hogfish Bar & Grill - ‬1 min walk
  • ‪El Mocho's - ‬10 min walk
  • ‪Hurricane Hole Marina - ‬4 min drive
  • ‪Starbucks - ‬5 min drive

Frequently asked questions

Is Living the Dream Key West Style pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at Living the Dream Key West Style?

As of Nov 8, 2026, prices found for a 1-night stay for 2 adults at Living the Dream Key West Style on Nov 9, 2026 start from $456, 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?

Onsite parking is available at the property.

What time is check-in at Living the Dream Key West Style?

Check-in begins at 3:00 PM.

What time is check-out at Living the Dream Key West Style?

Check-out is at 11:00 AM.

Where is Living the Dream Key West Style located?

Situated in Key West, this houseboat is within 2 mi (3 km) of Stock Island Yacht Club & Marina, Robbie's, and Key West Tropical Forest and Botanical Garden. Florida Keys Community College Library and Clark Maxwell Environmental Habitat are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 60 out of 63 reviews
Rating 8 - Good. 2 out of 63 reviews
Rating 6 - Okay. 0 out of 63 reviews
Rating 4 - Poor. 1 out of 63 reviews
Rating 2 - Terrible. 0 out of 63 reviews

9.6/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

9.4/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
6 of us spent the weekend on board and it was excellent. The boat was clean and well equipped. The hosts,Glen and Abby were terrific and were always there if needed. We look forward to returning soon
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great would definitely stay again
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Friendly host and unique location
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was excellent, awesome host, beautiful vacation!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a super nice and really neat older boat that gives you that live aboard charm.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a special stay and the hosts were incredibly helpful and friendly! Went above and beyond to make our stay nice.
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Glenn and Abby were fantastic host. Their hospitality was above any other host we have ever stayed with.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The stay was great! The host was extremely friendly and helpful. We will be back!
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

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

Great getaway

Great hosts and great accommodations!
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great, Experiece was awesome, would definitely recommend to anyone.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful. Glen and Abby were super friendly and welcoming. The boat was very comfortable and we enjoyed the marina area.
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities
Everything was very nice. Staff was friendly and helpful .
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
All around great time. Glen and Abby couldnt be better
Stayed 9 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
everything was perfect
Stayed 9 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The hosts were exceptional.
Stayed 5 nights in Sep 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Disliked: Location
Great boat. Sunset cruise was great. Only downside was it wasn’t in the best neighborhood.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Glenn was super welcoming and a cool dude. Very accommodating. Great location and beautiful marina. Hope to check it out again!
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect. Communication, location, the boat itself. And the host hot tub was a great bonus. Super relaxing trip!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
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!
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Wonderful spot, great hosts. Spectacular sunset cruise aboard Serenity.
Stayed 2 nights in Feb 2025
Tell us how we can improve our siteShare feedback