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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7

(2,413 Reviews)

Page 10 of 20 • 461 listings

Sailing live aboard Charter in Montego Bay, Jamaica

Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0

$950/day

60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

Powerboats in Bávaro · 200 guests

60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

New

Superowner

Best of 2026

$16/hour

Sail from Delray Beach to Lake Boca

Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0

Superowner

$125+/hour

Private Catamaran in Punta Cana – Natural Pool & Beach Stop

Sailing in Bávaro · 37 guests

Private Catamaran in Punta Cana – Natural Pool & Beach Stop

New

$250+/hour

Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia

Events in Bávaro · 200 guests

Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia

New

Superowner

Best of 2026

$17/hour

Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

Events in Miami · 14 guests

Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

New

$350/hour

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New

$332/hour

Private 52ft Catamaran Charter in St. Maarten with Lunch & Open Bar

Caribbean · 8 guests

Private 52ft Catamaran Charter in St. Maarten with Lunch & Open Bar

New

$700/hour

🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️

Powerboats in Punta Cana · 500 guests

🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️

New

Superowner

Best of 2026

$15/hour

Private 41' Power Catamaran Cartagena in Rosario Islands & Cholón

Sailing in Cartagena · 20 guests

Private 41' Power Catamaran Cartagena in Rosario Islands & Cholón

New

$340/hour

Luxury 52 Catamaran With AC - Price include 2 People

Sailing in Guna Yala Comarca · 8 guests

Luxury 52 Catamaran With AC - Price include 2 People

5.0

$2,700/day

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New

Superowner

Best of 2026

$75/hour

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

Events in Bávaro · 100 guests

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

5.0

$240/hour

Maxicat 65ft Private Party Catamaran in Cartagena

Sailing in Cartagena · 80 guests

Maxicat 65ft Private Party Catamaran in Cartagena

New

Superowner

$838/hour

Private 6-Hour Sailing Catamaran Charter in Punta Cana – Esmeralda

Sailing in Bávaro · 60 guests

Private 6-Hour Sailing Catamaran Charter in Punta Cana – Esmeralda

New

$265+/hour

Private 60ft Party Catamaran to Isla Catalina from La Romana – up to 65 Guests

Powerboats in La Romana · 65 guests

Private 60ft Party Catamaran to Isla Catalina from La Romana – up to 65 Guests

New

$3,750/day

Punta Cana - FAMILY BOAT

Sailing in Bávaro · 200 guests

Punta Cana - FAMILY BOAT

New

$160/hour

An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

Sailing in Cartagena · 23 guests

An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

New

Superowner

$231/hour

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

Sailing in Cartagena · 15 guests

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

New

$3,799/day

Instant Book

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

Sailing in Barrio Las Yaguitas · 80 guests

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

1.0

Superowner

Best of 2026

$183/hour

Private Catamaran Sosúa – 4 Hours, BBQ Lunch, Drinks, Snorkel & Hotel Pickup

Powerboats in Sosúa · 15 guests

Private Catamaran Sosúa – 4 Hours, BBQ Lunch, Drinks, Snorkel & Hotel Pickup

New

$1,149/day

Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

Sailing in Cartagena · 80 guests

Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

New

Superowner

$5,000/day

56' Lagoon Catamaran From St-Martin

Sailing in Saint Martin · 22 guests

56' Lagoon Catamaran From St-Martin

New

$561/hour

Private Catamaran Ocho Rios – Dunn's River Falls, Snorkel & Open Bar, up to 20

Powerboats in Ocho Rios · 60 guests

Private Catamaran Ocho Rios – Dunn's River Falls, Snorkel & Open Bar, up to 20

New

$4,190/day

Top Destinations Nearby

Sailing Reviews in Caribbean

DP
Dawn

Luxury 52 Catamaran With AC - Price include 2 People
⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!
Lisa

Sailing live aboard Charter in Montego Bay, Jamaica
It was my first time using the service and Chris was always available when I had a question. My clients had a great time.
Evan

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
Amazing people to deal with ! Highly recommend

Real reviews from happy Getmyboaters.

4.9 out of 5! 500,000+ reviews

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