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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8

(2,289 Reviews)

Page 11 of 18 • 428 listings

Sailing in Miami Beach · 42 guests

50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

New

Superowner

Best of 2026

$850/hour

Sailing in St. Thomas · 6 guests

46' Monohull Sailing Private Charter in Charlotte Amalie

New

$200/hour

Powerboats in Sosúa · 20 guests

Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ

New

$265/hour

Sailing in Punta Cana · 25 guests

😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran

New

$113/hour

Sailing in Cartagena · 12 guests

Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

New

Superowner

$150/hour

Sailing in Anse Marcel · 20 guests

St. Barth Boat tour with Lagoon 450 Cruising Catamaran!

New

$3,124/day

Powerboats in Ocho Rios · 100 guests

Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

New

$817/hour

Sailing in Cartagena · 8 guests

Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat

New

Superowner

$1,220/day

Sailing in Cartagena · 10 guests

Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

New

Superowner

$163/hour

Sailing in Montego Bay · 60 guests

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

New

$1,176/hour

Powerboats in Punta Cana · 65 guests

Punta Cana 60' Private Luxury Power Catamaran to Catalina Island

New

$471/hour

Events in Montego Bay · 10 guests

Montego Bay All-inclusive Yacht Experience

New

Superowner

$998/hour

Powerboats in Cartagena · 25 guests

Deal of the Week! Leopard 43 Ft Catamaran for Rent in Cartagena, Colombia.

New

Superowner

Best of 2026

$654/hour

Instant Book

Powerboats in Ocho Rios · 100 guests

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

New

$654/hour

Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

5.0

$115/hour

Sailing in Fajardo · 6 guests

Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

5.0

$450/hour

Sailing in Nassau · 10 guests

Lagoon 62’ 2019 Cruising Catamaran Rental in Nassau, New Providence

New

Superowner

$1,331/hour

Sailing in Negril · 100 guests

Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

New

$1,800/hour

Sailing in Nassau · 12 guests

3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests

New

$4,800/hour

Sailing in Bávaro · 60 guests

Private Catamaran Tour in Punta Cana: Party Boat+Snorkeling

New

$180+/hour

Events in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

New

Superowner

$750+/hour

Sailing in Bávaro · 100 guests

Fun Memories, Captain & Crew Included

New

Superowner

Best of 2026

$100/hour

Sailing in Nassau · 9 guests

Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests

New

$3,715+/night

Events in Sosúa · 18 guests

😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

New

Superowner

Best of 2026

$75/hour

Top Destinations Nearby

Sailing Reviews in Caribbean

Antonio

23’ Bayliner Beautiful Boat In Miami
¡Tuvimos una experiencia absolutamente increíble! Alquilamos el Bayliner de 23 pies para ir a Catalina y no pudo ser mejor. El barco está en excelentes condiciones, es muy cómodo y perfecto para un día de aventura en el mar. Lo que realmente marcó la diferencia fue el servicio de Catalina. Desde el primer contacto hasta el final de la renta, fue sumamente amable, profesional y atenta a cada detalle. Nos brindó toda la confianza necesaria para disfrutar del viaje sin preocupaciones. Si estás buscando una experiencia impecable en el agua, no dudes en reservar con ella. ¡Gracias por todo, definitivamente volveremos!
Alexander

23’ Bayliner Beautiful Boat In Miami
Great experience! The boat was clean, comfortable, and exactly as described. The captain was professional and friendly. Would definitely book again.
TL
Tanya

46' Monohull Sailing Private Charter in Charlotte Amalie
Captain Fancy and Lindsey were awesome!! We loved every minute of it. Pedro the pirate dog was so sweet. I would post pictures but not sure how. I don’t see an option.
Nathan

Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico
Great day on the water with a great crew! Service was excellent, food was very good and the boat is comfortable and clean. Really fantastic way to spend a day in PR!
Nathan

Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico
Beautiful, comfortable boat with a great sound system and excellent food! The captain and crew were great hosts and we enjoyed every minute of our day!