Boat holiday rentals in Stock Island

Romantic Captain's Quarters

Create unforgettable memories and experience a one-of-a-kind getaway on this classic Hans Christian sailboat, a true Picasso on the water! Docked at the stunning Perry Marina and Resort, your stay promises adventure and romance. Unleash your creativity with provided art supplies and musical instruments. Take advantage of resort amenities: two swimming pools, three restaurants, shuttle service to downtown, parking, happy hour, and concierge services for outdoor activities. Book your escape today!

The Seaside Boathouse

Experience a one-of-a-kind stay aboard the Seaside Experience. This stylish and spacious floating oasis offers a unique blend of modern comfort and waterfront tranquility. With well-appointed interiors, including a fully equipped kitchen, cozy bedrooms, and a welcoming living area, you'll find relaxation at every turn. Step out onto the deck to savor picturesque views or unwind under the sun. Perfect for a family retreat or a serene getaway with friends, this houseboat promises a memorable stay.

Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.

Beautiful 43 ' sportfish yacht

Come enjoy a yacht stay at Stock Island Yacht Club! Gorgeous facilities with Beach, pool, bar, and a gym!. The boat does not go out during the booking, but we can arrange a charter on it or other boats. We also rent street legal golf carts, outboard boats, and private backcountry sandbar charters. Come enjoy paradise on the Lisa Lynn! The marina has a small but gorgeous beach, amazing pool, and great tiki hut area. The tiki is at the end of a mangrove boardwalk, great place for a morning walk!

Gypsy Soul sleepaboard

Gypsy Soul is a 2017 42’ Lagoon sailing catamaran located at the beautiful Perry Hotel & Marina. She is steps away from 2 restaurants, 2 pools, laundry, showers. The Captain, Lisa (me), lives aboard with her mini schnauzer Ryder so when you stay we will be sharing the galley and salon area with us. Just staying on a boat in the Keys is a fabulous way to fully experience the area. Hot water shower onboard. *DISCLAIMER: If u have mobility issues, this spot may not be for u. See photos of entry.*

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Make Memories and Enjoy Sunsets on Euphoria

PLEASE READ ALL THE SECTIONS IN THE LISTING. 31ft BOAT ANCHORED at 1.5 mile off Key West NOT IN A MARINA. Transportation to the boat by water shuttle, fee not included in stay. REMEMBER ITS A BOAT, FUN EXCITING, ACCEPTANCE OF TRANSIENCE AND IMPERFECTIONS. THE AESTHETIC IS SOMETIMES DESCRIBED AS ONE OF APPRECIATING BEAUTY THAT IS IMPERFECT, IMPERMANENT AND INCOMPLETE IN NATURE. Embracing simplicity, nature imperfection and find joy, peace that nothing is perfect in this world. Enjoy Life

Amazing 33ft sailboat. Sail, stay and play.

This hidden gem offers you a sail, stay and play experience like no other. You will have an excellent location for the first and last night on the dock and then the rest in the beautiful waters of key west. Dinghy transportation will be provided as well as 2 tandem kayaks. This sailboat can sleep 4 but best fits 2. It has a bathroom with shower onboard. There is a fresh seafood market on property and a grill at your boat. Experience key west like a local. Bikes available to guests on shore.

60' Hatteras Motor Yacht

60' motor yacht stays docked panoramic waterfront views sunsets, kitchen large comfortable salon, Bar, top deck overlooks the entire bay, sleeps 2 in a stateroom with Queen Bed, in-suite head and shower WIFI and streaming television movie stations, Parking. Central Air, live aboard Crew outdoor entrance to their Cabin and a well-behaved small hypo-allergenic poodle. keeping the ships system operating smoothly, & common area clean, and providing safety highly trained in hospitality service.

Just Chillin' Out on the Ocean: 1/2 Off Charters!

Live your dream of sleeping out on on the ocean in a deluxe cabin cruiser yacht. Yacht "Just Chillin" features two state rooms each with comfy queen beds, two full bathrooms, A/C, hot water, high speed internet, covered patio, full dining , kitchen, living rooms and more! The yacht is anchored out on the ocean: see unbelievable waterfront sunsets and wildlife right from the boat! Enjoy this unique experience! All charter guests receive 2-for-1 water shuttles for their stay! Welcome Aboard!

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

Sail, Snorkel, Relax!

Why not add a little adventure to your trip? Experience something different with life aboard a 45' sailing yacht. You and yours will share the Master Cabin, with queen-sized berth and large attached head (bathroom with shower). Safely moored offshore in a protected harbor, enjoy quiet privacy as the boat swings gently with the wind and tides, free from mosquitos and no-see-ums. Sailing, fishing, paddle boarding, and snorkeling is offered at additional cost. Inquire for details.