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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,316 Reviews)

Page 6 of 19454 listings

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
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
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/hour
Board our Azimut Flybridge 42' for an unforgettable experience!
Events in Miami Beach · 13 guests

Board our Azimut Flybridge 42' for an unforgettable experience!

5.0
$200/hour
All Inclusive 40' Catamaran Sailing Experience - Old San Juan
Sailing in San Juan · 6 guests

All Inclusive 40' Catamaran Sailing Experience - Old San Juan

3.0
$725/hour
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/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
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
Curacao Private Sunset Tour Deluxe
Sailing in Jan Thiel · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)
Powerboats in El Cortecito · 100 guests

Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)

New
$373+/hour
44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos
Sailing in Leeward Settlement · 18 guests

44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos

5.0
$999+/hour
Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)
Sailing in Bávaro · 15 guests

Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)

5.0
$250/hour
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/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
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/hour
Instant Book
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/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
!!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
57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
Sailing in Fort Lauderdale · 12 guests

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

5.0
$450/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
Isla Saona Private Yacht – Luxury Full-Day Tour
Powerboats in Bávaro · 20 guests

Isla Saona Private Yacht – Luxury Full-Day Tour

1.0
$1,820/day
Instant Book
AMAR IS THE WAY TO ENJOY
Events in Miami · 13 guests

AMAR IS THE WAY TO ENJOY

5.0
Superowner
$400+/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
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

Sailing Reviews in Caribbean

  1. KF

    Katisha

    Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

    José and team were wonderful. They were responsive, accommodating and went the extra mile to make my clients 40th Birthday a great one! Will definitely use them in the future.

  2. Michael

    Michael

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

    My family had a wonderful day on The Bubble! Catherine and Serge responded quickly to our inquiries and were very accommodating of a request to change the time. They made us feel at home on the boat and the boat was great. They have a table outside and inside with seating, and a large area in the front to lounge. There have yoga mats and blankets we used and a speaker you can connect to. We were able to put our food in a fridge and a cooler. They provided water bottles. We enjoyed a fun ride in their dingy to go see the stilt houses in the bay as well. If you’re able to go on The Bubble at sunset you may be treated as we were to a gorgeous sunset over the water in addition to the great view of Miami lit up. Our captain Doug was great-super nice and professional and interesting to speak to him about the places he has lived all over the world. I highly recommend The Bubble!

  3. AD

    Alison

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

    We had such an amazing time on the Bubble for my bachelorette party! The boat is huge and was very stable on the bay - no one got sea sick! We were able to sail the whole time except leaving the dock. Captain Serge made sure we had a great time and also made sure we were all super safe onboard. The main bathroom is very large for a boat and clean. We also loved hanging out on the floating mat in the water! I highly recommend and would love to sail on the Bubble again!

  4. LH

    Laura

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

    We had a great experience on the boat. Captain is super kind, helpful and even very entertaining for a child we had on board. Very fun crew and a very pleasant day, route and atmosphere. Boat has all you need for a short or long term rental. Thanks for having us!

  5. AD

    Amanda

    Saint Kitts Private Boat Charter

    Ricky and his crew were fabulous! We had a mixup on where to meet which led to us being late. Ricky handled things so professionally and they made the day so fun and perfect! The boat and equipment were pristine, snorkeling was so fun and Ricky’s chocolate cake was the best! Highly recommend this private charter where your group has the boat to themselves with the best captain and crew!

  6. AM

    Andrew

    Saint Kitts Private Boat Charter

    What an amazing day! Ricky and JJ were absolutely amazing captain and host. We had 16 of us with not one complaint and most said this was the highlight of the cruise. They made sure everyone was happy and having fun. I would recommend to everyone.