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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7

(2,411 Reviews)

Page 12 of 20 • 460 listings

Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

Sailing in El Cortecito · 70 guests

Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

New

$644/hour

Instant Book

Private 50ft Catamaran to Saona or Catalina – Full Day

Powerboats in La Romana · 20 guests

Private 50ft Catamaran to Saona or Catalina – Full Day

New

$1,999/day

Instant Book

BOOK NOW 🏆 5-Star Private Luxury Yacht: All-Inclusive Captain & Crew

Water Sports in Macao · 110 guests

BOOK NOW 🏆 5-Star Private Luxury Yacht: All-Inclusive Captain & Crew

New

Superowner

Best of 2026

$17/hour

Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida

Sailing in Fort Lauderdale · 12 guests

Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida

New

$355/hour

Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!

Powerboats in Bávaro · 50 guests

Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!

New

$1,480/day

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

Sailing in Nassau · 10 guests

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

New

Superowner

$1,331/hour

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

Sailing in Cartagena · 8 guests

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

New

Superowner

$1,220/day

All inclusive Bali 4.4 Luxury Catamaran Charter

Sailing in Nassau · 10 guests

All inclusive Bali 4.4 Luxury Catamaran Charter

New

$720/hour

Private Aruba Catamaran Cruise – Open Bar, Snorkeling & Sunset (Up to 45 Guests)

Sailing in Oranjestad-West · 45 guests

Private Aruba Catamaran Cruise – Open Bar, Snorkeling & Sunset (Up to 45 Guests)

New

$764+/hour

Twin Island Paradise Snorkel Tour

Tours in Basseterre · 45 guests

Twin Island Paradise Snorkel Tour

New

$29/hour

Private 47ft Catamaran Fajardo for up to 44 Guests – Lunch, Open Bar & Snorkel

Sailing in Fajardo · 44 guests

Private 47ft Catamaran Fajardo for up to 44 Guests – Lunch, Open Bar & Snorkel

New

$4,950/day

💥 51' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥

Powerboats in Cartagena · 35 guests

💥 51' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥

New

Superowner

Best of 2026

$422+/hour

Instant Book

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

Sailing in Saint Martin · 8 guests

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

5.0

$1,000/day

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

Sailing in Fajardo · 6 guests

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

5.0

$450/hour

Montego Bay All-inclusive Yacht Experience

Events in Montego Bay · 10 guests

Montego Bay All-inclusive Yacht Experience

New

Superowner

$998/hour

Cruising Catamaran Charter in Cabarete, Dominican Republic

Sailing in Cabarete · 80 guests

Cruising Catamaran Charter in Cabarete, Dominican Republic

New

Superowner

Best of 2026

$400/hour

39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

Events in Bávaro · 12 guests

39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

New

$1,910/day

Punta Cana - PARTY BOAT (ADULT ONLY)

Sailing in Bávaro · 200 guests

Punta Cana - PARTY BOAT (ADULT ONLY)

New

$984/hour

Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo

Sailing in Fajardo · 12 guests

Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo

New

$699/hour

Hunter 450 Passage Yacht - Sail From Key Biscayne

Sailing in Key Biscayne · 10 guests

Hunter 450 Passage Yacht - Sail From Key Biscayne

New

Superowner

$250/hour

Private 80-Guest Sailing Catamaran Charter to Cayo Levantado

Sailing in El Centro · 80 guests

Private 80-Guest Sailing Catamaran Charter to Cayo Levantado

New

$450/hour

Private 26ft Family Friendly Speedboat Charter in Aruba

Powerboats in Oranjestad-West · 10 guests

Private 26ft Family Friendly Speedboat Charter in Aruba

New

$200/hour

Instant Book

4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana

Events in Punta Cana · 150 guests

4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana

New

$50/hour

Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

Sailing in Saint Martin · 20 guests

Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

New

$2,786/day

Top Destinations Nearby

Sailing Reviews in Caribbean

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!
AS
Aaron

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
Great time sailing with Robert in Sxm. Food and drinks were great. Only on the boat for two nights but got a lot done for the amount of time we had available.
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!
MC
Michael

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
Wonderful day. Highly recommend.

Real reviews from happy Getmyboaters.

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