Waterfront, Pool, Dock, Kayaks & Stunning Views

Welcome to Hook, Wine & Sinker, a beautifully designed 3-bedroom, 2-bathroom ground-level waterfront, pet-friendly home where comfort meets convenience in the heart of the Florida Keys. Overlooking the peaceful waters of Boot Key Harbor, this spacious getaway is perfect for families or small groups, with a maximum occupancy of 8 guests. Sleeping arrangements include 2 king bedrooms and 1 bedroom with 2 twin beds — there is no pullout couch.

Step outside to your private backyard and enjoy uninterrupted harbor views while lounging poolside, playing cornhole with friends, or casting a line from your private dock. Boaters will appreciate 40’ of usable dock space (dock is 25’ with room for overhang), perfect for bringing your vessel along for the adventure. Whether you’re arriving with a boat, trailer, or extra vehicles, there’s ample parking — plus a deep freezer and commercial ice maker to keep your catch fresh.

The screened lanai offers shaded dining with scenic water views, easily accessible from both the carport and the living area. Inside, you’ll find an open living space with plenty of comfortable seating, perfect for relaxing after a day in the sun. The updated kitchen features a large island with seating for eight — ideal for casual bites, wine tastings, or family-style meals.

When it’s time to wind down, the peaceful primary suite features a king bed and a calming atmosphere. A second king bedroom offers equal comfort for guests, while the third bedroom provides a fun, dorm-style space with twin beds perfect for kids or extra visitors.

Located near shopping, dining, and popular Keys attractions, Hook, Wine & Sinker has everything you need for a relaxing and activity-filled vacation.

Home Features:

3 Bedrooms | 2 Bathrooms | Sleeps up to 8 guests



(2 king beds, 2 twin beds, no pullout couch)



Private dock with 40’ usable space (25’ dock with room for overhang)



Pool with lounge seating



Screened lanai with outdoor dining



Propane grill



Cornhole boards



Deep freezer & commercial ice maker



Two single kayaks and one tandem kayak



Fully equipped kitchen: refrigerator, oven, microwave, drip coffee maker, tea kettle, and utensils



Ample parking for trailer and 4 vehicles



Ring doorbell for added security







*"Linen fee" is non negotiable damage waiver.

* Security cameras around the exterior of the home

* Pool heat/chill is available for an additional $200 per week (plus tax), and $28.57 per additional day (plus tax) thereafter.

*Pet Fee is $150 per pet. Max of 2, 50lb max. (PLEASE DO NOT ALLOW YOUR PETS ON TO ANY BEDS OR LIVING ROOM FURNITURE. IF PET HAIR IS FOUND IN ANY OF THE BEDS AND FURNITURES THERE WILL BE AN EXTRA FEE CHARGED. THE FEE WILL BE THE AMOUNT OF THE ORIGINAL CLEANING FEE.)

*3.9% Cancellation fee applies to ALL cancellations.

*Please note that a signed guest agreement is required prior to check-in. To facilitate this, we will need an email address to send the DocuSign document.

* We provide a complimentary starter pack of paper towel, toilet paper, dish & laundry detergent, dish soap, bar soap, trash bags & dish sponge.

*Max occupancy is the number of occupants the City allows and does not guarantee beds for that number. Please read the bedroom and bed descriptions thoroughly.

*Seasonal Seaweed Notice: Like much of the Florida Keys, our canal can experience seaweed at certain times of the year. On the ocean side, this usually happens in summer/fall while gulf-side canals see it more in winter/spring. It’s a natural part of the area and may affect the canal during your stay.

* This home may only be available from Saturday – Saturday during peak season.

*VACA-25-138