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All listings in Montego Bay

Great sailboat rentals near Montego Bay, St. James Parish.

Page 1 of 111 listings

2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$995/hour
Limited Availability
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Superowner
Best of 2025
$659/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$834/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
Best of 2025
$933/hour
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
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
Montego Bay All-inclusive Yacht Experience
Events in Montego Bay · 10 guests

Montego Bay All-inclusive Yacht Experience

New
Superowner
Best of 2025
$998/hour
Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat
Sailing in Montego Bay · 14 guests

Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat

New
$250/hour
Ultra luxe Full Day Yacht Charter to Negril!
Events in Montego Bay · 10 guests

Ultra luxe Full Day Yacht Charter to Negril!

New
Superowner
Best of 2025
$1,625/hour
Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New
Snoozed - Active 02 Oct 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

Sailing Reviews in Montego Bay

  1. PW

    Portia

    46 feet luxury yacht in Montego Bay with round trip transportation!

    This is a great yacht company for celebrations! Communication was great from start to finish from pick up to returning back to the resort. My party of 12 had a great time and I really appreciated the birthday decorations and birthday cake provided from the crew!

  2. VM

    Vera

    46 feet luxury yacht in Montego Bay with round trip transportation!

    My friends and I had an amazing experience and would definitely recommend. Everyone was extremely accommodating and kind. The yacht was absolutely beautiful and exceeded our expectations. We had the time of our lives.

  3. AG

    Akeem

    46 feet luxury yacht in Montego Bay with round trip transportation!

    Service was impeccable. Exceeded our expectation! Food was amazing. Boat was clean. Had a damn good time. The whole crew was friendly & made sure everyone in our group was great!!!

  4. Ed

    Ed

    3hr Classic Yacht Experience Montego Bay

    The crew of the vessel was very professional, entertaining, and engaging. The food and beverage services were exceptional, to say the least. I highly recommend this boat.

  5. LB

    LaNeisha

    46 feet luxury yacht in Montego Bay with round trip transportation!

    To say “we had a great time” is an UNDERSTATEMENT! Knot Stressin has made my husband’s 40th birthday one for the books! With limited time to prepare, Deidrick and his crew created a memorable experience for our party group. We were able to host a magnificent party boat experience for our family and can’t wait to celebrate again. We will definitely use you guys again! Thanks!! 🫶🏾

  6. SA

    Sarina

    46 feet luxury yacht in Montego Bay with round trip transportation!

    Deidrick was great at communicating and my group felt very safe with Desmond and crew on board