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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,245 Reviews)

Page 35 of 35839 listings

1986 22ft Catalina Sailboat in Holland, Michigan
Sailing in Holland · 6 guests

1986 22ft Catalina Sailboat in Holland, Michigan

New
$75+/hour
Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!
Events in Milwaukee · 30 guests

Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!

New
$500/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
High Demand
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
Snoozed - Active 02 Jan 2026
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
Snoozed - Active 01 Jul 2025
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
Snoozed - Active 08 Jul 2025
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
Snoozed - Active 02 Jan 2026
Brand new 200HP bayliner VR5
Powerboats in Texas · 7 guests

Brand new 200HP bayliner VR5

5.0
Snoozed - Active 08 Jul 2025
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Sep 2025
Luxury 40" Sail Catamaran | Cozy Winter Sail | San Francisco
Sailing in Marina del Rey · 12 guests

Luxury 40" Sail Catamaran | Cozy Winter Sail | San Francisco

5.0
Snoozed - Active 02 Jul 2025
Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons
Sailing in Lacey Township · 6 guests

Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons

5.0
Snoozed - Active 02 Jan 2026
Luxury Sailing Yacht Charter
Events in Zona Comercial · 6 guests

Luxury Sailing Yacht Charter

New
Superowner
Snoozed - Active 02 Aug 2025
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
Snoozed - Active 24 Jul 2025
Catamaran boat Party La Paz
Events in Zona Comercial · 12 guests

Catamaran boat Party La Paz

New
Superowner
Snoozed - Active 17 Oct 2025
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 Aug 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 Aug 2025
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
Herreshoff 12 1/2 Sailboat Charter
Sailing in North Haven · 3 guests

Herreshoff 12 1/2 Sailboat Charter

New
Snoozed - Active 28 Sep 2025

Sailing Reviews in United States

  1. JE

    Joshua

    Brand new 200HP bayliner VR5

    This was my first experience renting a boat. I hired Dylan to captain it. He hosted us for my daughter's birthday party and everything went better than I anticipated. Dylan was professional, courteous, and patient from start to finish. I wouldn't hesitate to book him again.

  2. CC

    Christine

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Richard was prompt and affordable. We really enjoyed our day out. There should be mention of the wear and tear on the boat and the fact that the depth finder was broken. Kind of an issue when navigation in such shallow water. Luckily we have experience with that but those who do not may have an issue.

  3. CB

    Christine

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Great value and very efficient communication. The day we rented a boat was very windy. Richard provided a pontoon with a higher horsepower motor - it made our day much more enjoyable. We will definitely reach out to rent from Richard next time we are in FLA!

  4. LS

    Leighanna

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    My family and I had a blast! we celebrated my birthday and this was an awesome time. Richard was quick to respond, fantastic price point, made drop off and pick up so easy, and all around amazing great guy. Don't hesitate to book as you will be thrilled that you did! **Remember an aux cord to hook up your device to listen to music**

  5. MB

    Mark

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.

  6. SB

    Scott

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    What a day on the water! Our Group of 7 people had an awesome time Captain Brian & Erin. The Catamaran was huge! The sun deck and the interior were clean and full of amenities. The Sailing around Sag Harbor and Shelter Island was something that we will never forget.