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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,105 Reviews)

Page 1 of 16382 listings

🏆BEST 2024🏆 Luxurious & elegant yacht designed for maximum comfort rent me!
Events in Bávaro · 80 guests

🏆BEST 2024🏆 Luxurious & elegant yacht designed for maximum comfort rent me!

4.3
Superowner
$117/hour
Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$195/hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
Best of 2025
$600/hour
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2025
$675/day
 Summer Rates, Limited Time!!!!!!, Set Sail on the Caribbean Seas
Sailing in Gros Islet · 12 guests

Summer Rates, Limited Time!!!!!!, Set Sail on the Caribbean Seas

4.9
$100/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2025
$200/hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Superowner
Best of 2025
$659/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95+/hour
Lagoon 450 Sailing Catamaran Charter in Saint Martin Community
Sailing in Anse Marcel · 20 guests

Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

4.9
$1,872/day
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
$155+/hour
Instant Book
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
$200/hour
MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 40 guests

MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
Superowner
Best of 2025
$1,100/day
The 30ft in Cruises at Barbados
Sailing in Welches · 12 guests

The 30ft in Cruises at Barbados

5.0
$180+/hour
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

4.8
$550/day
Catamaran in Saint George's
Sailing in Saint George's · 55 guests

Catamaran in Saint George's

4.8
$176+/hour
Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew
Sailing in Miami · 42 guests

Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew

5.0
Superowner
Best of 2025
$800/hour
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

5.0
$1,395/day
Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends
Sailing in Simpson Bay · 20 guests

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

5.0
$2,106/day
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
Sailing in Cartagena · 16 guests

Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

4.8
Superowner
Best of 2025
$970/day
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
The Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8
Superowner
Best of 2025
$800/hour
Instant Book
🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.
Events in Barrio Las Yaguitas · 150 guests

🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.

5.0
$160/hour
🏝️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

Sailing Reviews in Caribbean

  1. JF

    Jorge

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Great experience with great hosts. Nice boat took us out to Palomino and Icacos, and the family had a blast. Great music, snacks, and beverages were on point. Overall, it exceeded my expectations. Will definitely book again with Jose and team.

  2. Stephanie

    Stephanie

    Luxury 48' Leopard Catamaran in Cartagena

    Absolutely PERFECT!!! What a beautiful way to spend a day on this gorgeous boat with some of the friendliest staff. Reserved for our 1 year anniversary by far the best event we did while in Cartagena

  3. AL

    Alexandra

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    We had an amazing time with Jose! He was incredibly welcoming and constantly made sure we were enjoying ourselves. We'll definitely be booking with him again on our next visit!

  4. Khadijah

    Khadijah

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    This experience and trip was beyond amazing ! Especially with the help of Amory and his crew. I highly recommend booking this charter ! This definitely was the peak of my birthday ! Te amo

  5. PW

    Portia

    46 feet luxury yacht in Montego Bay with round trip transportation!

    This is a great yacht company for celebrations! Communication was great from start to finish from pick up to returning back to the resort. My party of 12 had a great time and I really appreciated the birthday decorations and birthday cake provided from the crew!

  6. HN

    Hope

    Sail away in Montego Bay! 39ft Leopard Catamaran

    My friends and I had an amazing charter for my birthday! Stacey communicated every step of the way. She even arranged for me to have my favorite color balloons and a cake! I’d highly recommend using her for your next charter, I certainly will!