Vacation rentals in Stock Island

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy ice-cold AC, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 sparkling pools & hammock park, 2 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Live the island life w full access to all resort amenities. Your tropical escape awaits! This memorable place is anything but ordinary.

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. 🛥️🌴🎣

Sailboat Stay + Resort Amenities

Unplug and unwind 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, luxury touches, and the comforts of home, this is where island adventure meets peaceful retreat.

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Stella on Stock Island

Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and you'll find yourself welcomed into an inviting living space. The living area transitions into a kitchen complete with essential appliances. Down the hall from the living area lies the bedroom offering a peaceful haven for rest and relaxation after a day spent exploring. An elegantly appointed bathroom awaits, featuring modern fixtures and amenities. Queen Bed & Sofa Bed

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.

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Great Ocean Views! No regrets

Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. There is a little something for everyone from adventure seekers, to people who just want to get away and enjoy island life. You will see all kinds of sea life including a manatee from time to time! From deck view gorgeous sunsets, various sea birds catching their meals and even a military jet formation on occasion. Many great areas to kayak/paddle board off the boa.

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

Rooster Camper at Leo's

Our charming Rooster Camper in Stock Island is the perfect spot for your Key West getaway. Fully furnished, it offers a comfortable bed and a kitchenette with essential amenities for a relaxing stay. Located just two blocks from the entrance to Key West, you can easily bike, scooter, or take a golf cart into town. This camper is set inside Leo’s RV Park, and guests can enjoy shared amenities during their stay. For the comfort of all guests, pets are not allowed.

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.