Boat vacation rentals in Caribbean

Cozy Sailboat at the Montains (air conditioned)

Escape to the unique & enchanting "Mountain Sailboat Retreat," anchored in the mountains of Cayey & Cidra, Puerto Rico. Imagine the beauty of a sailboat combined with the tranquility of mountain landscapes, offering an unforgettable stay for nature enthusiasts & adventure seekers alike. Guests will have the chance to stay on a beautiful sailboat, providing a charming & distinctive experience. The interior offers a comfortable sleeping area, a cozy living room, & all amenities for a great stay.

Stay on Roxie with FREE anytime cancellation!

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. 🛥️🌴🎣

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.

All Inclusive! Snorkel • Sail • Sun & Fun

Stay aboard our 42’ Lagoon 420 catamaran anchored off downtown Key West. Hosted by Captain Dan, a 10-year Superhost, your all-inclusive stay includes snorkeling, sailing, spear fishing, and fishing gear. Relax in the private queen cabin with ensuite bath, enjoy the fully equipped galley, and unwind in the air-conditioned salon. Quick dinghy rides bring you to Key West’s vibrant dining and nightlife. Your perfect floating island escape!

Graceland Boathouse Treehouse, Closed for Stays

GRACELAND IS NO LONGER AVAILABLE FOR STAYS. Graceland hosted happy travelers from Oct 2021 to April 2025. All proceeds went to a local nonprofit. Situated conveniently on Las Olas, this 1979 remodeled vintage double cabin is a hidden gem in an exotic location. The boat has 2.5 cabins & 2 en-suite full bathrooms. Host lives onsite and available as & when needed. Boat has one Toshiba air conditioning unit and multiple air movers/fans.

Exceptional stay on a boat in Sainte-Anne

Do you dream of sea air, beauty, and romance? Then come live at anchor in the beautiful Caritan Bay, in Sainte-Anne. No experience is required. You can swim, hike, or kayak, read, or relax at any time, rocked by the waves and surrounded by turtles. With the easy-to-handle 3.5hp tender, you can reach the nearby pontoon and explore the island. The very quiet Caritan Bay is ideally located near the pretty village of Sainte-Anne.

Ocean Life (boathouse)

Disfruta una estadía única en OceanLife, un yate totalmente equipado para tu comodidad. Vive la experiencia de despertar sobre el agua, con todas las amenidades esenciales. La embarcación permanece anclada en el muelle en todo momento, brindando seguridad y tranquilidad durante tu visita. Ideal para una escapada diferente y relajante en la costa.

Private 45’ Luxury Yacht

45’ Luxury Yacht docked in beautiful Boot Key Harbor. The yacht remains at the dock during your stay. This is not a charter for cruising. Amazing sunrises and sunsets while enjoying happy hour lounging on the bow of this yacht. Fully enclosed, or open, dining on the spacious aft deck

Vacation on a Yacht near Peanut Island

Private 50’ yacht in a boat slip near Peanut Island. World class snorkeling, swimming, sun bathing and sand bar wading in Palm Beach. 2 staterooms, 2 full bathrooms, large sun deck, cockpit. Sleeps 4, or 6 for an additional fee. Comes with ice, water, coffee.