Holiday rentals with an EV charger in Stock Island

Stay on the Water with Southernmost Serenity

Experience a unique Key West getaway aboard a comfortable boat docked at the beautiful Perry Hotel & Marina on Stock Island. Enjoy waterfront living with resort-style amenities while staying just minutes from downtown Key West. The boat offers a cozy and functional space designed for relaxing after a day exploring the island or spending time on the water. Inside, you’ll find comfortable sleeping accommodations and convenient essentials for an easy and memorable 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: there is no oven on board.) Perry Hotel & Marina Amenities - 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 - On-site private bathroom Dining & Drinks Nearby - Matt’s Stock Island Kitchen & Bar - Salty Oyster Dockside Bar & Grill Getting Around - Complimentary hourly shuttle to downtown Key West - 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.

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 your 🚢 boat.

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.

The Twin Palm Villas - A

Indulge in island luxury at this stylish 2BR/2BA canal front oasis just blocks from Sombrero Beach. Located in a newly renovated duplex, this light-filled unit features coastal-modern design, plush bedding, a chef-ready kitchen, and a breezy outdoor patio overlooking the water. Wake up to tranquil canal views, or stroll to the white sands of Sombrero Beach. Whether you’re here to relax, boat, fish, or explore, this upscale hideaway delivers serenity and style in the heart of Marathon.

Spacious lux home, private pool/spa, 80' dock

Sunchasers Paradise has everything you are looking for and more in a spacious canal-front home. It's the perfect place to have your next company or couples retreat or reconnect with extended family. Play and relax in the private pool or spa under the palms swaying in the costal breeze. Sunchasers Paradise is the ideal spot for fishing, watersports, and beach lovers. Enjoy this luxury home with endless amenities, nearby dining, and day trip adventures. Unforgettable moments await!

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 & will accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St, jet ski re

Keys Cove-

Our Keys Cove is a high-rise home with magnificent ocean views. It is located in a fabulous resort community 23 miles from Key West. Our oversized "Parrots Perch" offers a stunning sunrise and sunset experience. Dock your boat on our 43-foot seawall equipped with padded posts and whips. Enjoy the resort amenities including pickleball tennis courts, a huge pool, hot tub, marina, tiki beach, kayaking, and more. Be sure to read our guidebook for the best places to see.

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!

Key West • The Harbor House • Luxury Sea Charters

Harbor House Welcome to a completely different way to stay in Key West. This hybrid boat + house experience blends the comfort of a waterfront home with the unmistakable energy of being on the water. This isn’t a cruise. This isn’t a typical rental. This is dockside luxury. Set directly on the water and connected to the Luxury Sea Charters fleet, this is your dockside escape with the option to turn your stay into a full on-the-water experience.

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

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.

Waterfront, dock, easy ocean access, heated pool!

Keys living at its best! Tropical classy, comfy and private – yet easy access to everything you could want. This 2 bedroom, 2 bathroom home on a quiet dead end street with open views and ocean access (with houses only on one side) in the heart of the heart of the Keys comes with all the amenities, complete with private pool and ample parking. Please contact prior to submitting booking request. Thank you!