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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,950 Reviews)

Page 3 of 16374 listings

Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island
Tours in Fajardo · 6 guests

Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

5.0
Superowner
Best of 2025
$1,500/day
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Instant Book
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
Best of 2025
$960/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
Best of 2025
$1,000/day
Luxury Lagoon 440 Sailing Catamaran in Key West
Sailing in Key West · 6 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0
$250/hour
Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
Powerboats in Fort Lauderdale · 6 guests

Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

4.8
Superowner
$113+/hour
Instant Book
 46' Oyster Sailboat in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

46' Oyster Sailboat in St. Thomas, Virgin Islands

5.0
$197+/hour
sunbathe and relax on our island in the middle of the ocean
Events in Punta Cana · 100 guests

sunbathe and relax on our island in the middle of the ocean

3.7
Superowner
Best of 2025
$50/hour
48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0
$187+/hour
🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Instant Book
🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
Events in Sosúa · 150 guests

🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

4.4
$300/hour
Luxury Private Catamaran Charter – All-Inclusive from St. Maarten
Sailing in Cole Bay · 16 guests

Luxury Private Catamaran Charter – All-Inclusive from St. Maarten

5.0
$2,095/day
Sailing Catamaran Yacht for up to 24 Guests in Aruba
Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 24 Guests in Aruba

4.6
Superowner
Best of 2025
$600/hour
Instant Book
Discover Miami on this Sea Ray Yacht Charter
Events in Miami · 13 guests

Discover Miami on this Sea Ray Yacht Charter

5.0
$90/hour
DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY
Events in Uvero Alto · 80 guests

DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY

5.0
$50/hour
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,650/day
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.5
Superowner
$125+/hour
Charter Beneteau Oceanis 440 in Saint Lucia private sailing cruise
Sailing in Gros Islet · 9 guests

Charter Beneteau Oceanis 440 in Saint Lucia private sailing cruise

5.0
$1,133/day
Marlowe Hunter 33’ Sailing in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing in Fort Lauderdale

5.0
$90+/hour
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2025
$50/hour

Sailing Reviews in Caribbean

  1. AF

    Angela

    Sailing Catamaran Yacht for up to 24 Guests in Aruba

    Book it!! Hands down the best crew ever! I had a group of 18 and everyone enjoyed themselves. The crew is very attentive and entertaining. I would highly recommend them. Thanks again guys!!!

  2. DL

    Dmitriy

    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

    Highly recommend. We booked a day trip with Jose to Culebra Island (Flamenco beach) and really enjoyed the amazing day. The captain and the mate made our day exciting and unforgettable. There are a lot of beach toys, chairs, snorkeling gears, drinks and snacks on the boat, so you don't need to care about it. For extras you may get a bbq and/or a Seabob, which is cool underwater scooter. Will definitely book again.

  3. PC

    Peter

    Sailing Hobie Cat Rental in Noord, Aruba

    Lisa was a great host as she welcomed us and got us squared away with the 16 ft Hobie Cat w/jib! The whole experience was incredible and we got some great speed on the Hobie Cat. It was a high wind day (25-30 mph) and we couldn’t have asked for a better time on the water. Lisa was gracious, helpful, and fun!

  4. DG

    Darla

    21ft Sun Tracker 20 Party Barge {Catch a Vibe}

    Our group of 6 had the BEST time with Captain Porshia! The communication was phenomenal, she called the day before to discuss our desired itinerary, meet location, and any needs we may have. We had a prompt departure, and Porshia was very knowledgeable of boating and the area. Porshia was not only friendly but also very helpful and made sure all of our needs were taking care of. 10/10… HIGHLY RECOMMEND!!! We will definitely be back.

  5. AW

    Alexandra

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    Our tip was amazing! The crew was incredible and they made sure we had a great time. Rebecca's meal was wonderful! We had a blast on the jetski, visiting the pigs, and dancing, as well as being able to relax and enjoy the sun. Thank you for making sure we all had the best day. I highly recommend booking with Rebecca! Communication was great and she was so accommodating. Thank you!

  6. AW

    Alice

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    Rebecca and Max were excellent friendly hosts! The tour around the islands were phenomenal with the perfect amount of time between the islands and the food prepared by Rebecca was phenomenal. For a relaxing trip on a super clean and spacious cataraman, this is highly recommended.