Boat vacation rentals in West Indies

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. 🛥️🌴🎣

Casa O Carbonera Lux Boutique House

Welcome to Casa O Carbonera! Immerse yourself in luxury at this new 4-story haven in San Diego's enchanting Walled City. Designed by the renowned architect Vladimir Caballero, our house accommodates 12 guests with utmost comfort. Enjoy complimentary one airport transport, delicious breakfast, and attentive housekeepers. Elevate your stay with optional catering, entertainment, and exciting tours. Your unforgettable getaway awaits! Book now and create beautiful memories at Casa O Carbonera.

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.

Unusual accommodation in Deshaies

Welcome aboard Mayelu, a comfortable 12-meter catamaran anchored in the beautiful bay of Deshaies, Enjoy the serenity and amenities of life on board, in the heart of the world's largest swimming pool: the Caribbean Sea. 2 comfortable and well-ventilated double cabins 2 bathrooms (No hot water but it's 30°) Equipped kitchen, A cozy salon A large cockpit A trampoline, suspended above the water, ideal for reading or taking a nap.

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.

Mariners 210 Great Location with Marina Views

Best Vacation rental to explore the Florida Keys 3/3 bedroom Villa facing the marina with ocean views and steps away from the best pool by the ocean in the FL keys, 2 king master bedrooms with ensuite bathrooms, 2 pools, 2 hot tubs, gym, tennis, indoor and outdoor pickleball, recreation room with pool table, foosball, ping pong and card table.

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