Houseboat holiday rentals in Caribbean

Baycation Houseboat | Florida Keys Waterfront Stay

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

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. 🛥️🌴🎣

Sea Chateau ~ Jupiter Motor Yacht

Our 44' Gibson cabin-yacht is docked on the banks of the old Jupiter River, a tropical paradise. (down and two upstair landings). 2/2 with three beds. On waterside, queen bed and full bath (shower). Below deck is second brm (2 full beds and its own full bath (shower). Tropical vegetation. No wake zone. Occasional paddleboards and slow-mo small boats. Being here makes the heart brighter and the soul lighter. It's a Zen experience you'll notice the relaxing results the second you step aboard.

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.

Escape to Pineapple

Escape to a houseboat near Stocking Island, Exuma, where staying onboard is part of the adventure! Moored close to Chat and Chill beach bar, you're just steps away from all the fun. But when you want peace and quiet, Stocking Island’s beautiful, secluded beaches are right at your doorstep. Dive into the clear waters for snorkeling, paddleboarding, and spotting sea turtles and tropical fish. It’s the perfect place for relaxation and adventure! Upgrade to the Boston Whaler to explore further!

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

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

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.

Modern Houseboat On the water

This cozy houseboat is located at Sunset Bay Marina & Anchorage in Stuart, FL. A short 5-minute walk takes you to Historic Down Town Stuart and all of its fabulous shops and restaurants. Here at the marina, we have Sailors Return restaurant and Gilbert's Coffee Bar to satisfy any craving you have. Martin County’s beautiful beaches are just 6 miles away. Two bicycles are at your disposal for enjoyable rides.

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.

Aqua Villa Houseboat "Dolphin" with upper deck

Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get much more unique than this! Welcome to The Aqua Villas at Mangrove Marina Resorts... “Dolphin” houseboat, located between Key Largo and Islamorada in Tavernier at Mile Marker 91.7 on the Bayside, in a protected tranquil oasis cove of Community Harbor, in the beautiful Florida Keys.

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.