Experience life on the water with a unique Key West stay aboard a comfortable yacht docked at the beautiful Perry Hotel & Marina on Stock Island. Enjoy ocean breezes, waterfront sunsets, and resort-style amenities while staying just minutes from the energy of downtown Key West.
The boat offers a comfortable and inviting space designed for relaxing after a day exploring the island, chasing sunsets, or enjoying life on the water. Inside, you’ll find cozy sleeping accommodations, thoughtful essentials, and everything you need for an easy, memorable Key West stay.
*Please note that the sofa bed in the salon is actually a convertible dinette. Additional details below.
Boat Features - Comfortable sleeping areas (two bedrooms that sleep four comfortably, plus a convertible dinette in the salon that will sleep another 1-2 guests comfortably) - Induction cooktop for simple meals - Microwave - Electric toilets for added comfort - Cozy interior living space - Unique waterfront stay experience (Please note: for safety, the propane powered oven in the galley has been unhooked and is not functioning.)
Perry Hotel & Marina Amenities - Private marina showers and bathrooms to compliment the shower and bathrooms on the boat itself - Two outdoor resort-style pools - 24-hour fitness center - Yoga classes - On-site dog parks - Water sports and excursions (jet ski tours, fishing charters, sunset sails) - On-site laundry
Dining & Drinks Nearby - Matt’s Stock Island Kitchen & Bar - Salty Oyster Dockside Bar & Grill
Getting Around - Complimentary shuttle to and from Old Town Key West every half hour - Easy access to Duval Street, beaches, restaurants, and nightlife - Valet or self-parking available at the marina (self-parking is free)
Whether you’re visiting for sunshine, boating adventures, or the vibrant Key West atmosphere, this marina stay offers a fun and memorable way to experience the island.
Come live like the Songs You Know By Heart
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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 Fort Zachary Taylor Historic State Park. Key West Tropical Forest and Botanical Garden and Sails To Rails Museum at Flagler Station are also worth visiting.
Key West Tropical Forest and Botanical Garden - 2 min drive - 2.1 km
Key West Naval Station - 3 min drive - 3.7 km
Duval Street - 15 min drive - 8.7 km
Getting around
Key West, FL (EYW-Key West Intl.) - 8 min drive
Restaurants
Hogfish Bar & Grill - 19 min walk
Hurricane Hole Marina - 4 min drive
Bad Boy Taqueria & Tequila - 1 min walk
Toasted Coconut - 4 min drive
El Siboney Stock Island - 7 min walk
Frequently asked questions
Does Wake Up On the Water with Southernmost Serenity have a pool?
Yes, this property has a pool.
How much does it cost to stay at Wake Up On the Water with Southernmost Serenity?
As of 20 May 2026, prices found for a 1-night stay for 2 adults at Wake Up On the Water with Southernmost Serenity on 11 June 2026 start from NZ$320, 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.
Is Wake Up On the Water with Southernmost Serenity pet-friendly?
Yes, this houseboat allows dogs (limit 2 total).
What time is check-in at Wake Up On the Water with Southernmost Serenity?
Check-in begins at 4:00 PM.
What time is check-out at Wake Up On the Water with Southernmost Serenity?
Checkout is at 10:00 AM.
Where is Wake Up On the Water with Southernmost Serenity located?
Situated on the waterfront, this houseboat is within 1 mile (2 km) of Robbie's and Key West Tropical Forest and Botanical Garden. Stock Island Yacht Club & Marina and Lower Keys Medical Center are also within 2 miles (3 km).