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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,353 Reviews)

Page 6 of 38912 listings

Premium Sunset Sailing on a True WestSail 43ft Yacht
Sailing in San Diego · 6 guests

Premium Sunset Sailing on a True WestSail 43ft Yacht

5.0
$200/hour
45' Sea Ray Yacht Charter in Turks & Caicos
Powerboats in The Bight Settlement · 15 guests

45' Sea Ray Yacht Charter in Turks & Caicos

5.0
$550/hour
Fountaine Pajot Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Fountaine Pajot Great Sailing Catamaran for up to 25 people!

4.5
Superowner
$1,600/day
47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay
Sailing in Seabrook · 12 guests

47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

5.0
$300/hour
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

4.9
$107+/hour
Suncatcher 22ft Family Pontoon!
Powerboats in Montana · 8 guests

Suncatcher 22ft Family Pontoon!

5.0
$65/hour
High Demand
Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!
Sailing in Marina del Rey · 12 guests

Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!

4.8
$275+/hour
Private 44ft Trimaran in Los Cabos for 50 Guests
Sailing in Juárez · 50 guests

Private 44ft Trimaran in Los Cabos for 50 Guests

5.0
Superowner
Best of 2026
$250/hour
44' Luxury Cruiser Sailboat Charter  | San Francisco Bay
Sailing in Alameda · 6 guests

44' Luxury Cruiser Sailboat Charter | San Francisco Bay

5.0
$159/hour
40' Sea Ray Sundancer All-Inclusive Yacht Charter in Riviera Maya.
Events in Puerto Aventuras · 12 guests

40' Sea Ray Sundancer All-Inclusive Yacht Charter in Riviera Maya.

5.0
Superowner
Best of 2026
$350/hour
Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
Sailing in Chicago · 10 guests

Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

5.0
Superowner
$250/hour
Instant Book
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
Private Harbor Cruise in Newport Beach, California
Tours in Newport Beach · 4 guests

Private Harbor Cruise in Newport Beach, California

5.0
$200/hour
81' Sailboat | Hot Tub + Full Water Toys | Up to 50 Guests
Sailing in Marina Vallarta · 50 guests

81' Sailboat | Hot Tub + Full Water Toys | Up to 50 Guests

New
$603/hour
Lovely Catalina 36 Sailboat in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Lovely Catalina 36 Sailboat in Puerto Vallarta

5.0
Superowner
$155/hour
Limited Availability
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
Superowner
$355/hour
Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$240/hour
Exclusive Sailing Boat
Sailing in Marina Vallarta · 15 guests

Exclusive Sailing Boat

5.0
Superowner
Best of 2026
$78+/hour
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/hour
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/hour
50' Azimut All-Inclusive Yacht Charter in Playa del Carmen.
Events in Playa del Carmen · 20 guests

50' Azimut All-Inclusive Yacht Charter in Playa del Carmen.

4.9
Superowner
Best of 2026
$420/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
42ft Catalina MkII Sailing Yacht in The San Diego Bay, California
Sailing in San Diego · 6 guests

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

5.0
$285/hour

Sailing Reviews in United States

  1. ST

    Shaddy

    56' SeaRay Yacht in New York!

    We had an incredible experience aboard Encore with Captain Max! I booked the boat for my engagement, and when rain threatened our original date, Max was extremely understanding and worked with me to move the reservation so the moment could still be everything I had planned. He was communicative, flexible, and genuinely invested in helping make the occasion special. The boat was beautiful, clean, comfortable, and exactly as advertised. Once we were aboard, Max made us feel completely at ease and gave us the perfect experience on the water. This was one of the most important and memorable days of our lives, and Max played a huge role in making it happen. I truly appreciate how accommodating he was throughout the entire process. I couldn’t recommend Captain Max and Encore more highly!

  2. TA

    Ty

    Suncatcher 22ft Family Pontoon!

    We had a great experience renting this pontoon. The host was incredibly accommodating, flexible, and communicative from start to finish. The listing was exactly as advertised, and everything on the boat worked perfectly. The pickup and dropoff was easy. We’d definitely rent from them again!

  3. KS

    Kevin

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    What an amazing trip. I’ve been coming to the waters on the Vineyard for years and Mason took us to places I’ve never seen before. The boat was perfect for a relaxing adventure. I would highly recommend for almost any type of group from a couple to a family or a small group. What an experience !

  4. SV

    Stacey

    42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

    Nate is truly the best of the best if you’re looking to book a boating experience! There are individuals who distinctly stand out for good reason and Nate is one of them through and through.

  5. AT

    Anthony

    47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

    Booked Captain Terry's boat for my wife's birthday. Everything went perfectly!! Captain Terry suggested a sunset cruise and plotted out a great itinerary. We ended up singing happy birthday as the sunset in the background. The boat itself was beautiful and very stable. For those who get seasick, the boat does not rock very much. Captain Terry and his First mate Wayne were fantastic. Very friendly and took care of everything. This boat is all about having a great time with your friends!

  6. Damion

    Damion

    47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

    Cpt Terry and his crew were awesome! They were very knowledgeable about the local history and showed us fantastic hospitality!!! We had nine people in our party to celebrate my wife’s 50th Birthday and everyone had a total blast!!! We’ll definitely book with Cpt Terry again!!!