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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,125 Reviews)

Page 2 of 17397 listings

The Midnight Sun,  Affordable Luxury  motor yacht
Events in Oranjestad-East · 15 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0
Superowner
Best of 2025
$450/hour
Instant Book
Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0
$129+/hour
Caribbean Island-hopping
Sailing in Le Marin · 10 guests

Caribbean Island-hopping

New
$15+/night
Instant Book
🏝️Exciting Private Yacht: Affordable Charter with Crew🎉
Powerboats in Punta Cana · 250 guests

🏝️Exciting Private Yacht: Affordable Charter with Crew🎉

3.0
Superowner
$117/hour
38’ Lagoon Catamaran Charter In Miami, Florida
Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0
$299/hour
Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Great Sailing Catamaran for up to 25 people!

4.3
Superowner
Best of 2025
$980/day
Luxury Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Catamaran located in Downtown Miami

5.0
$219+/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$995/hour
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
Instant Book
Leopard 47 PC Power Catamaran Charter in Castries, St Lucia
Events in Castries · 8 guests

Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

4.9
Best of 2025
$313/hour
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725/hour
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
$97/hour
Charter 45ft Cruising Catamaran In Christchurch, Barbados
Sailing in Welches · 26 guests

Charter 45ft Cruising Catamaran In Christchurch, Barbados

5.0
$250/hour
Sail Away In Negril With 39ft Leopard Catamaran
Sailing in Negril · 16 guests

Sail Away In Negril With 39ft Leopard Catamaran

5.0
Superowner
Best of 2025
$900/hour
All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island
Sailing in Nassau · 12 guests

All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island

5.0
$600/hour
Instant Book
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
Sailing in Henrys · 20 guests

44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

5.0
$207/hour
Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates
Sailing in Miami · 49 guests

Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates

5.0
Superowner
Best of 2025
$800/hour
Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands
Sailing in West Bay · 15 guests

Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands

5.0
$350/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$834/hour
🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana
Powerboats in Punta Cana · 80 guests

🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana

4.5
$85/hour
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
Best of 2025
$933/hour
“Exclusive Escape, Unlimited Adventure on our Yacht”
Events in Miami · 14 guests

“Exclusive Escape, Unlimited Adventure on our Yacht”

5.0
$250/hour
Instant Book
44' Cruising Monohull Charter in Kralendijk, Caribbean Netherlands
Sailing in Kralendijk · 14 guests

44' Cruising Monohull Charter in Kralendijk, Caribbean Netherlands

5.0
$282/hour

Sailing Reviews in Caribbean

  1. EDDIE

    EDDIE

    All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island

    Ignacio was a wonderful host. He creates a good game plan for the day and makes the entire ride / day comfortable for all. I would definitely use him if we travel back to Nassau. This specific vessel is also perfect for a day charter for a group of 4 or more

  2. Marcus

    Marcus

    Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

    One of the most fantastic experiences we’ve ever been on. It was so good that we booked the next day as well thank you to the captain and crew. They were above expectations one of the best adventures we’ve ever been on. An absolute must in St. Lucia.

  3. Afolabi

    Afolabi

    “Exclusive Escape, Unlimited Adventure on our Yacht”

    This trip was top class a 10/10 , very respectful captain, good communication and professionalism at its highest . Really appreciate Carlos and the captain.

  4. Garry

    Garry

    The Midnight Sun, Affordable Luxury motor yacht

    My wife and I had a wonderful experience during our sunset cruise! Jesus and crew did an amazing job hosting us..will look to book again if ever in Aruba 🌵😃

  5. Michael

    Michael

    Private Luxury Sailing Experience out of Old San Juan

    Had a fantastic time! Willy and David were perfect and our entire group had an incredible experience. Definitely book!!

  6. Bountiful

    Bountiful

    The Midnight Sun, Affordable Luxury motor yacht

    Incredible Experience Despite the Rain (first time seeing this in Aruba) – Huge Thanks to Captain Jesus & Crew! We booked our boat charter in Aruba through Getmyboat, and even though the weather didn’t fully cooperate (heavy rain!), the experience was still unforgettable thanks to the amazing crew. Captain Jesus is legit – super professional, flexible, and went above and beyond to make sure our group had a great time despite the conditions. The crew was incredibly accommodating and positive the whole time, which made a huge difference. We even brought a DJ on board, and they welcomed it with no issues – it turned into a really fun and unique vibe on the water. The boat was clean, well-maintained, and had plenty of space for our group to relax and enjoy ourselves. Would absolutely recommend this charter to anyone visiting Aruba – rain or shine, they’ll take care of you!