Houseboat holiday rentals in Key West

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. 🛥️🌴🎣

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Two Bedroom Aqua Lodge! Dolphin

Key Colony Marina offers dual stateroom brand new Aqualodges for weekly and monthly rentals. Each Aqualodge has a fully equipped kitchen, living room, 2 bedrooms, Includes access to the BEAUTIFUL Cabana Club! Direct TV Stream, WIFI, and A/C. Check in 3:00PM and check out 11:00 AM. Boat Rentals, bike rentals, kayak & paddle board rentals, fishing charters on site, bait and tackle shop. Everything you need to experience the best of the Keys. No smoking. Four people max sorry no infants allowed.

The Salty Sunshine of Key West

Anchored in one of Key West's most serene and protected bays, the Salty Sunshine invites you to embark on a getaway or gather with friends for unforgettable memories in this vibrant island paradise. Experience the magic of Key West as the sun rises and sets uniquely over the shimmering waters of the Southernmost City. Enjoy unobstructed 360-degree views from the comfort of our top deck, coffee, sunrise, wine, sunset. Cherished memories that last a lifetime. Water taxi transportation needed.

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

Happys Houseboat

Looking for a unique and unforgettable vacation experience in Key West? Look no further than this charming houseboat listed on Airbnb! Escape the ordinary and indulge in the tranquility of living on the water. Our houseboat offers all the comforts of a cozy home, with the added bonus of breathtaking views and a prime location. Included in the rental is use of a skiff to get to and from land and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

Adventurers escape breathtaking off-grid houseboat

Get ready to indulge in a relaxing and unforgettable experience at the original houseboat getaway! 🌴What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! enjoy breathtaking sunsets and a private sanctuary perched above the sea. 😍 Don't miss out on this one of a kind experience Book your stay now and create memories that will last a lifetime

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.

Glamorous Houseboat Stay @ The Perry

Welcome to the Enchantress. This modern houseboat has been handcrafted to provide a warm and wholehearted True Key West experience, perfect for couples seeking a romantic getaway. Featuring a contemporary design and sleek interiors, a stylish retreat with stunning water views. Enjoy the rooftop, where you can soak in a 360° view of the waters, or unwind in the fresh Queen -size bed. With a modern kitchennette and resort amenities, indulge in comfort and luxury during your stay.

2 Bedroom Aqualodge # 11 Grouper

This 2 Bedroom Aqualodge is an adorable accommodation in the Old Wooden Bridge Resort and Marina. You are able to enjoy the resort amenities during your stay. Beautiful Salt Water pool, Fish Cleaning Stations. Renters can also bring their boat or rent a boat from OWB at an additional fee. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool to use for your swimming pleasure. This is a marina with houseboats and rental boats in the slips.

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

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.