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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,357 Reviews)

Page 6 of 19440 listings

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
$960/hour
Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!
Events in Bávaro · 200 guests

Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!

5.0
Superowner
Best of 2026
$17/hour
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,700/day
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!
Events in Bávaro · 100 guests

2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!

New
Superowner
Best of 2026
$117/hour
Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)
Sailing in Bávaro · 15 guests

Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)

5.0
$250/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Limited Availability
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Deerfield Beach · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
$350/hour
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

5.0
$1,560/hour
Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI
Sailing in Charlotte Amalie · 12 guests

Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

5.0
$293/hour
Limited Availability
Exclusive Escape with Ocean Explorer Catamaran in Punta Cana
Powerboats in Uvero Alto · 30 guests

Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

4.8
Superowner
Best of 2026
$16/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran
Sailing in Charlotte Amalie · 12 guests

Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

4.6
$365/hour
🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana
Tours in Punta Cana · 100 guests

🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana

3.7
Superowner
Best of 2026
$50/hour
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉
Sailing in Uvero Alto · 30 guests

Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉

3.5
Superowner
Best of 2026
$100/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Santa Barbara Plantation · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
$220/hour
Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 12 guests

Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico

5.0
$800/hour
60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!
Powerboats in Bávaro · 200 guests

60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

New
Superowner
Best of 2026
$16/hour
All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths
Caribbean · 12 guests

All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths

5.0
$2,334+/day

Sailing Reviews in Caribbean

  1. Shawn

    Shawn

    Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

    We had a great time on the Pisces. Captain Judi and Callia were a great crew to be with. They took us to two different snorkeling spots that were great. Callia looked after us in the water and followed us to make sure we were all safe and got back to the boat. She also makes a great, and strong, Pisces punch. The Pisces was in great shape and fit my family of 10 very comfortably. Next time we are in St Thomas I will certainly book with them again.

  2. 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!

  3. 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.

  4. SW

    Sarah

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

    Amura and her crew were above and beyond anything we could have hoped for in our sailing. Truly 5 star from our arrival to our departure. The day could not have been any better executed for parents and for kids… and THAT is a hard feat! First of all- no surprises, the boat is actually as amazing as it looks!! So many listings seem great but on arrival are not the case. Not here!!! The boat is in pristine condition with various areas to gather The Crew- what can we say… the kindness, patience, humor, knowledge… all of it!! They kept our champagne glasses and surf and turf plates full!! The food was top notch, from fruit, to charcuterie to our meal and dessert. Delicious!! Rebecca even helped to accommodate some dietary needs… so grateful The Day- captain Max lead us on an adventure to see the best and most beautiful parts of the Bahamas. All in all, you cannot go wrong with Amura… from the boat to the crew this is a 5 start experience from start to finish.

  5. SN

    SOHAIL

    Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

    The supermarket is 5 minutes walk away. They will help take your purchases to the boat. The crew is fantastic.. my girlfriend drifted away on the paddle board when the tide turned. They had the boat moving in under 60 seconds to go catch her.. They are great

  6. PG

    Princess

    Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

    I am so happy I was able to book this yacht to celebrate my 30th birthday. In fact it was three of our birthday’s and we all thoroughly enjoyed our experience on the boat. The communication between myself and the owner was excellent especially since I went during the time of Cartagena’s curfew. The staff made great accommodations for my group. I was able to jet ski for the first time ☺️. I will definitely book this catamaran again the next time I visit Cartagena. Thank you so much for a wonderful experience.