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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,942 Reviews)

Page 16 of 16382 listings

Luperon: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options
Sailing in Puerto Plata Province · 8 guests

Luperon: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options

New
$85/hour
Instant Book
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Sailing in Grand Case · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$395/hour
Hobie Cat Rental on Cockleshell Bay
Sailing in Saint George Basseterre Parish · 1 guest

Hobie Cat Rental on Cockleshell Bay

New
$100/hour
Luxury Catamaran 52ft private charter for up to 40 people in Cartagena
Powerboats in Cartagena · 40 guests

Luxury Catamaran 52ft private charter for up to 40 people in Cartagena

New
$360/hour
7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne
Sailing in Grande-Terre · 8 guests

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

New
$1,160/day
"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands
Sailing in Pointe-a-Pitre · 6 guests

"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

New
$10,166/day
Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda
Sailing in English Harbour · 6 guests

Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

5.0
$920/day
Charter a Cruising Monohull in Foster Hall, Barbados
Sailing in Less Beholden · 15 guests

Charter a Cruising Monohull in Foster Hall, Barbados

New
$10,667/day
51' Neel Cruising Catamaran Rental in Le Marin, Martinique
Sailing in Rivière-Salée · 9 guests

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

New
$1,576/day
' Center Console in Frigate Bay
Basseterre · 6 guests

' Center Console in Frigate Bay

New
$113/hour
TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter
Sailing in Wickhams Cay 1 · 20 guests

TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

New
$3,000/day
The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel
Sailing in El Cortecito · 50 guests

The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel

New
$699/hour
Instant Book
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran
Sailing in Nassau · 12 guests

Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

4.9
Snoozed - Active 02 Mar 2026
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Snoozed - Active 20 Oct 2025
38’ Lagoon Catamaran Charter In Miami, Florida
Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0
Snoozed - Active 02 Jan 2026
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
Snoozed - Active 23 Jan 2026
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
Snoozed - Active 02 Apr 2026
Hanse 418 Cruising Monohull Rental in Hollywood, Florida
Sailing in Hollywood · 12 guests

Hanse 418 Cruising Monohull Rental in Hollywood, Florida

New
Snoozed - Active 02 Nov 2025
Private 65ft Catamaran for Charter Trips in Montego Bay
Sailing in Montego Bay · 40 guests

Private 65ft Catamaran for Charter Trips in Montego Bay

New
Snoozed - Active 02 Nov 2025
Leopard 46 Catamaran Sailing in Antigua & Barbuda
Sailing in English Harbour · 6 guests

Leopard 46 Catamaran Sailing in Antigua & Barbuda

New
Snoozed - Active 02 Mar 2026
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 31 Mar 2026

Sailing Reviews in Caribbean

  1. AA

    AKINLOLU

    Luxury Catamaran Lagoon 52' Capacity up to 40

    The Yacht tour was great. The size of the boat was perfect for my crew of 33. The food services provided was great, and Eddy the live saver saved a member of my group which helped avoid a situation. In all it was a good experience to have in Cartagena.

  2. MH

    Moe

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Our group of 9 had an amazing time on this cat! The sunset views are beautiful, the crew was very attentive, and we couldn’t have asked for more. 10/10 would book again!

  3. KN

    Karen

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I had ever used this app before, but glad I did! Johnathan had amazing communication prior to our charter and was very helpful and transparent of what was included and answered all of our questions. The crew was AMAZING too! We saw sea turtles, sunfish, and more! Found a gorgeous conch shell near Rose Island and the kids LOVED the slide. The food was also AMAZING and the fully stocked bar was a winner!!! Boat was incredible and they also has sea scooters!!!

  4. LB

    Leanna

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I truly cannot say enough great things about Anthony and Mile. From the moment we stepped on board, everything exceeded our expectations. The boat was absolutely stunning—beautifully maintained and equipped with all the fun extras that made the day unforgettable. The food was not only delicious but thoughtfully prepared and presented. Most importantly, the entire experience was filled with fun, laughter, and amazing memories. Every detail was perfect, and it was worth every single penny. Thank you both for an incredible day on the water—we’ll definitely be back!

  5. ES

    Erika

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    Anthony and Milei were beyond amazing. Beautiful persons and outstanding service! They made our trip an unforgettable experience.. We look forward to come back! The boat was neat, pretty and spacious. The food was over the top, and the drinks were delightful.

  6. MC

    Mev

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Thank you! Captain, crew and chef were all phenomenal! Attentive, helpful and polite - all around great experience! Highly recommend this boat and crew. We had a group of 10 adults and 10 teens. Everyone raved about our day with the Sea Warriors. Just book them for a fun, luxury experience that is customizable for your group. 5 stars all the way.