Vacation rentals with an EV charger in Stock Island

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.

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.

Hemingway First Floor Townhouse @ 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!

Sailboat Retreat | Resort Amenities

Step aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes and the comforts of home, this is where island adventure meets peaceful retreat.

Historic Key West - Cigar House - Sleeps 4

The neighborhood is alive, dynamic, and surrounded by Key West History - unquestionably the most intact Old Town Key West neighborhood on the island. There are excellent restaurants within walking distance, and Duval Street is only two blocks from the property - close enough, yet far enough away! Ft. Zachary Taylor, located only two blocks to the west of the property, is a National Historic Park and boasts the nicest beach with the best sunsets on the island.

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.

Poolside Suite with Direct Pool Access

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!

Duval Street Suites with full kitchen heated pool,

Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street in historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.