Boat vacation rentals in Caribbean

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Top-rated boat rentals in Caribbean

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Guest favorite

Boat in Fort Pierce

4.84 out of 5 average rating, 19 reviews

28 foot hunter sailboat

“Bumboat” is a 28 foot sailboat moored 50 yards off a beautiful beach in Fort Pierce Florida. Close to bars, restaurants, beach and downtown Fort Pierce. This is a “glamping” experience. Sleeps 4. Bathroom, fresh water, a/c, quiet Generator. 2 paddle boards included. A small dingy is provided for transport to and from the boat. Assistance with transport to the boat instruction on use of all amenities will be provided on check in. Runabout boat available ($70 day) ebikes available ($20 day)

Superhost

The interior of the sailboat features a cozy living area with two seating spaces adorned with colorful cushions. A blue table stands in the center, accompanied by a decorative vase filled with fresh greenery. Warm wooden accents create a welcoming atmosphere.

Boat in Cidra

4.87 out of 5 average rating, 210 reviews

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.

Guest favorite

A serene view of Bimini Bay is captured, featuring a sailboat docked at a wooden pier. Lush greenery lines the waterway, while additional boats are visible in the distance. The clear blue sky enhances the tranquil ambiance of the waterfront setting.

Cottage in Anna Maria

4.83 out of 5 average rating, 117 reviews

Sea Breeze in Anna Maria With Private Dock

Welcome to Sea Breeze, our newly renovated home which is the Second Floor of a 2-story property at the North-end of Anna Maria Island. It includes 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free Netflix, washer/dryer, and a full kitchen are available. You can sailboat directly to Bimini Bay, walk to Pine Ave and City Pier, or eat in nearby restaurants. Our private home has everything you need for a perfect beach vacation in AMI!

Superhost

A modern boat is docked at a marina, featuring a spacious deck with a canopy for shade. The hull reflects the surrounding water, and multiple boats can be seen in the background, alongside buildings lining the marina.

Boat in Le Gosier

4.86 out of 5 average rating, 29 reviews

Expérience unique sur un bateau

Expérience unique de séjour sur un bateau (fixé à la marina). Profitez des plus beaux couchers de soleil avec votre partenaire ou votre famille. Pour un plaisir en famille ou une soirée romantique. Situé à Le Gosier, Guadeloupe, à quelques pas des restaurants, bars, boite de nuit, pizzerias, boulangeries et un supermarché. Lavomatique, douches chaudes et WC à proximité sur la marina L'accès aux pontons est sécurisé. Vous disposerez d'un pass vous permettant d'ouvrir ponton et sanitaires.

Top guest favorite

The image captures a serene view from the deck of a sailboat, with calm water reflecting the clear sky. The shoreline is visible in the background, showcasing colorful houses and palm trees, contributing to a peaceful maritime atmosphere.

Boat in Key West

4.86 out of 5 average rating, 155 reviews

ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun

You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C throughout and plenty of room to relax down below. Every reservation comes with a sunset sail along with day sailing, snorkeling or fishing. Layout and be lazy on the spacious deck or whatever you would like to do! Visit SailAway GetAways on FB for more detailed view. **Unfortunately one night reservations do not allow time for excursions. Except a sunset sail.**

Top guest favorite

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

4.93 out of 5 average rating, 346 reviews

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.

Top guest favorite

A comfortable 12-meter catamaran is anchored in the serene waters of Deshaies Bay. The white hull contrasts with the blue sky and nearby greenery. The spacious design features two sails, with life rings affixed for safety. Other boats are visible in the background.

Boat in Deshaies

5 out of 5 average rating, 16 reviews

Hébergement insolite à Deshaies

Bienvenue à bord du Mayelu, un confortable catamaran de 12 mètres ancré dans la magnifique baie de Deshaies, Profitez de la sérénité et des commodités de la vie à bord, au cœur de la plus grande piscine du monde : la mer des Caraïbes. 2 cabines doubles confortables et bien ventilées 2 salles de bains (Pas d'eau chaude mais il fait 30 °) Une cuisine équipée, Un carré cosy Un grand cockpit Un trampoline, suspendu au-dessus de l’eau, idéal pour lire ou faire la sieste.

Guest favorite

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

4.91 out of 5 average rating, 182 reviews

Stay on the Roxie!

Enjoy, peaceful, ocean-breezy, star-filled nights, on the water! Free parking and free round trip transport 1 to & 1 from Roxie per night’s stay! Roxie is anchored in a protected, shallow 3-4ft lagoon. We live on a boat a half-mile away should you need anything. 😊 Roxie has a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters. No cooking but you may bring to go food, drinks. 🛥️🌴

Guest favorite

A sailboat is anchored on calm water, framed by lush green hills in the background. The boat features a yellow and white hull, with a green awning providing shade over the deck. The sky is clear, illuminated by soft sunlight.

Boat in Sainte-Anne

4.9 out of 5 average rating, 51 reviews

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.

Top guest favorite

A sailboat is anchored in calm waters during sunset, with vibrant orange and purple hues reflected on the surface. The silhouette of the boat, featuring a tall mast and a shaded cockpit area, contrasts against the colorful sky. Nearby boats are visible in the distance.

Boat in Miami

4.98 out of 5 average rating, 792 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Superhost

A luxury yacht is docked, featuring a spacious upper deck covered by a sunshade. The exterior showcases a light-colored hull with large windows and visible fenders. The marina backdrop includes multiple boats and a clear blue sky, enhancing the serene coastal setting.

Boat in Marathon

4.73 out of 5 average rating, 70 reviews

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