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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,472 Reviews)

Page 9 of 41 • 968 listings

Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
$100/hour
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in San Miguel de Cozumel · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$250+/hour
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$520/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

4.9
Superowner
$117+/hour
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/hour
Lux Catamaran Fountaine Pajot 40ft
Sailing in Leeward Settlement · 10 guests

Lux Catamaran Fountaine Pajot 40ft

New
$714+/hour
Limited Availability
Beneteau 36’ Cruising Monohull in Redondo Beach
Sailing in Redondo Beach · 6 guests

Beneteau 36’ Cruising Monohull in Redondo Beach

5.0
$125/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour
Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht
Sailing in San José del Cabo · 12 guests

Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht

5.0
$500+/hour
Day Sails and Sunset Cruises in Downtown St. Petersburg,  44' Morgan Sailboat
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

5.0
$206+/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way
Events in Cancún · 20 guests

Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way

4.8
$330/hour
Create Memories you will Cherish for Life on this 47' Luxury Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

5.0
Superowner
$225+/hour
Beatiful Catalina 42' Yacht Rental in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Beatiful Catalina 42' Yacht Rental in Puerto Vallarta

5.0
Superowner
$138+/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour

Sailing Reviews in United States

  1. Nick

    Nick

    Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

    Absolutely incredible experience from start to finish! Our captain was professional, knowledgeable, and made the entire afternoon on the water unforgettable. The boat was beautiful, the atmosphere was perfect, and every detail was taken care of. Whether you’re looking for a relaxing cruise or an amazing day sailing, I couldn’t recommend this experience more. Hands down a 10/10 experience, and we can’t wait to do it again!

  2. Peter

    Peter

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    My wife and I had a great time taking out Matt’s Sunfish sailboat! He was there to greet us and help prepare the boat, and he had great recommendations for where in the lake to find the best sailing conditions. His sunfish is well maintained and sailed great. I would love to rent his Sunfish again next summer!

  3. PH

    Paige

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    Had a great day out on Matthew’s lovely sunfish. Matt was very communicative and also offered us an alternative activity in case of no wind. Thankfully, the wind filled and my mom and I had a great day of sailing on beautiful MerryMeeting Lake! Matt was very pleasant to talk with and answered all of our questions about the area and the boat. We will definitely be back and would encourage others to rent this boat from Matt!

  4. KH

    Katherine

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    We had a fantastic experience renting Matt’s sunfish sailboat. He was easy to communicate with, gave excellent instructions, and the boat and lake were an absolute dream. He even pointed us towards a great local spot for ice cream/light bites after the sail. We will definitely be back to rent from Matt again!

  5. BE

    Bobby

    SeaDoo Switch Sport *5 ADULTS*

    The booking was seamless, the boat was clean and new, our host Kyle was 100% top notch. He thoroughly explained the operation of the boat and was very patient with our questions. He and his sister Brittany made sure our experience was a five star one.

  6. AR

    Allyah

    SeaDoo Switch Sport *5 ADULTS*

    Working with Kyle and his sister has been a very professional and awesome experience! Me and my fiancé arrived and the boat was already pulling up waiting for us at the dock! Kyle gave us both a very thorough review of everything on the boat and how it worked. He then proceeded to show us the controls of each button along with how to maneuver the boat proficiently and allowed us to drive while he was present just for any follow up questions and comfortability! The boat was an amazing experience and we enjoyed the whole day on the water with the tub may I add that was provided with the rope!! 10/10 recommended if you really want a full experience of Lake Texoma!! Thank you guys so much!!