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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,171 Reviews)

Page 18 of 18431 listings

Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina
Sailing in Gros Islet · 8 guests

Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

New
$729/night
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN IN SAINT MARTIN
Events in Marigot · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN IN SAINT MARTIN

New
$396/hour
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Sailing in Grand Case · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$396/hour
Sailing Yacht Charter with amazing crew all inclusive
Sailing in Panama City · 6 guests

Sailing Yacht Charter with amazing crew all inclusive

New
$885/night
Boston Whaler Center Console Rental in Road Town, Tortola
Powerboats in Wickhams Cay 1 · 10 guests

Boston Whaler Center Console Rental in Road Town, Tortola

New
$2,400/day
Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options
Sailing in Punta Cana · 8 guests

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

New
$85/hour
Instant Book
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
$1,165/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
$10,201/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
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
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
$1,581/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
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
' Center Console in Frigate Bay
Basseterre · 6 guests

' Center Console in Frigate Bay

New
$113/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/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
Snoozed - Active 02 Feb 2026
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
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
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. AJ

    Ashley

    Sail away in Montego Bay! 39ft Leopard Catamaran

    Words cannot express my gratitude towards this crew. I had been looking for private boat tours for my 30th birthday and came across this listing randomly. From day one Stacey was amazing with communication and answered any and every question that I had. The Crew was also top-tier once we got to Jamaica and on the boat. It felt like they were a part of the group. We laughed, had amazing food, had great drinks, and also several of us took a nap lol. The water was amazing and the vibes were even better. I definitely recommend this 100 times again.

  2. RH

    Ron

    Sail away in Montego Bay! 39ft Leopard Catamaran

    I rent private boats in many Caribbean islands but this has been one of the top 3 experiences ever. The captain Peter was great. With storm clouds in the sky he stayed in front of it so we would only see sun. The staff was super attentive yet gave us our space to be great. And the host Stacey is overly polite ! I plan on booking this boat everytime I go to Jamaica !

  3. LP

    Latoya

    Sail away in Montego Bay! 39ft Leopard Catamaran

    I booked with Stacey for my birthday trip to Jamaica and she did not disappoint. The boat was definitely big enough for my group of eight and there was nothing but good vibes from the crew. The snorkeling was a great addition to the beautiful views and smooth ride. We enjoyed the punch and snacks. I would Definitely book again.

  4. dwayne

    dwayne

    Sail away in Montego Bay! 39ft Leopard Catamaran

    Great day on the water! We had group of 14 people. Plenty of room to lay out and have a good time. Captain Peter and crew were awesome! The drinks stayed flowing, snorkeling was fun and beef patties for lunch were a nice touch! Would absolutely recommend!

  5. 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!!!

  6. 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!