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Wake Up On the Water with Southernmost Serenity

Experience life on the water with a unique Key West stay aboard a comfortable, cozy 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.) -Propane grill on the sundeck for grilling while watching the historic Key West sunset -Like many boats, entry is through a marine hatch with companionway steps. Most guests adjust quickly, but guests with limited mobility may find boarding more challenging. 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

AHOY & Welcome Aboard

FULL Usage of my turnkey & complete set up for 2-6 guests (MAX) staying on a safely docked & like new HUNTER 260 Sailboat at the PERRY HOTEL's PERRY MARINA ! AND full usage of ALL the Amenities of the distinguished PERRY HOTEL- FREE: Shuttles to K W 11am to 11pm-(1:00 am wknds), 2 pools, security patrols 24 /7 w gated entry, AT BOAT parking, plus 5 showers & rest rooms always cleaned , a coin laundry. + food and drinks. AND BEST OF ALL, being gently rocked to sleep on our Caribbean waters.

Waterfront Boat Stay + Resort Amenities

A Whim isn’t just a place to sleep—it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

Amazing Location 3bed/2bath & Swim Spa

Fully furnished ground floor cottage with 3 bedrooms (queen bed in each), 2 full bathrooms, plus a loft with an additional queen bed & twin bed. Full kitchen and laundry unit. Only a half block off of Duval Street midway between Mallory Square and the Southernmost Point. Less than a 2 minute walk to Ernest Hemingway's home and steps to dining, bars and shopping. Available for monthly rental. Use of the entire unit and shared outdoor space with a swim spa. Truly, a stylish & unique experience.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Tiny House | 35 min to KW + Free Parking & Pool

Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. Extra parking space is available for a fee.

Key West Treehouse Duplex Suite @ Suite Dreams Inn

Suite Dreams Inn is an intimate family-owned boutique Key West Bed & Breakfast in the tranquil upscale Casa Marina Old Town neighborhood, offering oversized suites with luxurious king & queen beds, kitchens, living rooms, 2 pools, 24/7 laundry, free parking, and relaxing outdoor spaces. We are LGTB & pet friendly & well accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St, jet ski re

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Pool View Suite | Beachside Resort

Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

Serenity by the Sea | La Brisa

Welcome to your island escape! This 2BR/2BA condo in the gated La Brisa complex is across from Smathers Beach and just a short ride to Duval Street. Enjoy an open-concept layout, coastal-chic décor, full kitchen, private balcony with salt pond views, and resort-style amenities including a 24-hr pool, hot tub, sauna, tennis, EV charging, and more. Perfect for beach days or exploring Key West—book your stay today!

Treehouse Private Village Barnacle Resort

Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This beachfront retreat offers plush rooms with ocean views, a private beach. For those seeking adventure, complimentary kayaks and bicycles are at your disposal. Here, you'll wake up to the sound of waves, and explore the coastal beauty, feeling like a million bucks each day.

King Room, Fairfield Inn, Close to Old Town

Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and the iconic Hemingway House. Unwind on Smathers Beach or take in the lively sunset celebrations at Mallory Square. Perfect for families, couples, and adventurers, with nearby snorkeling, dining, and cultural spots for a memorable island escape.