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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,250 Reviews)

Page 16 of 40950 listings

40 ft Spacious Catamaran
Sailing in Marina Vallarta · 12 guests

40 ft Spacious Catamaran

5.0
$545/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 8 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California
Sailing in Newport Beach · 6 guests

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

5.0
$160/hour
Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
Sailing in Manhattan · 6 guests

Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

5.0
$224+/hour
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2025
$75/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco
Sailing in San Francisco · 6 guests

Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco

5.0
$300/hour
Instant Book
42' Trimaran Rental in Cabo San Lucas, Mexico
Events in Marina · 45 guests

42' Trimaran Rental in Cabo San Lucas, Mexico

5.0
$720/hour
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/hour
Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
Best of 2025
$199/hour
Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos
Sailing in Leeward Settlement · 10 guests

Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos

5.0
$728+/hour
Romantic city lights trip on beanbags on 42 ft Bertram
Events in Long Beach · 6 guests

Romantic city lights trip on beanbags on 42 ft Bertram

5.0
$125/hour
Brand new 200HP bayliner VR5
Powerboats in Texas · 7 guests

Brand new 200HP bayliner VR5

5.0
$110/hour
Hinckley Pilot 35 Classic Sailboat in the Heart of NYC
Sailing in Manhattan · 6 guests

Hinckley Pilot 35 Classic Sailboat in the Heart of NYC

5.0
$330/hour
Instant Book
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
Best of 2025
$315+/hour
41ft Sailing Charters from Costa Mujeres, Cancun
Sailing in Isla Mujeres · 32 guests

41ft Sailing Charters from Costa Mujeres, Cancun

5.0
Superowner
Best of 2025
$248/hour
32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)
Sailing in Cleveland · 6 guests

32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)

5.0
$325+/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

4.8
$245/hour
43 ft Sealine. As clean as new
Events in Cancún · 14 guests

43 ft Sealine. As clean as new

5.0
$245/hour
Newport RI: Sailing, Swimming and Sightseeing
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing

5.0
$200/hour
CHEAP PONTOON BOAT RENTALS 8-12 PEOPLE
Water Sports in Huntersville · 12 guests

CHEAP PONTOON BOAT RENTALS 8-12 PEOPLE

New
$150/hour
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Sailing in North Vancouver · 10 guests

Charter Jeanneau 50 DS Sailing Yacht in English Bay

5.0
$359/hour
Lagoon 44’ with Open Bar and Full lunch.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch.

New
Superowner
$436/hour
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0
$150/hour

Sailing Reviews in United States

  1. Elisabeth

    Elisabeth

    Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

    Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

  2. KF

    Karly

    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

    We booked a 2 hour boat trip to celebrate my parents retirement and Francisco was amazing! The boat was beautiful, clean and exactly as listed. He was an incredibly gracious host and took us on a lovely sail! Will definitely be back!

  3. JM

    Julie

    No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

    Great vessel. Everything we needed! Amazing deck hand and Captain (Georgia and Matt). They made our air and water show experience incredible!

  4. NB

    Nicole

    20ft Bayliner VR5 Boat in Rockville, IN

    First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!

  5. WF

    Wayne

    40 ft Spacious Catamaran

    Kelly was professional and courteous for the booking and all questions that came afterward and very accommodating when we wanted to preview the boat, working with the caterer, etc. Captain Cesar and the entire crew were wonderful and very helpful during the entire trip. It was a great experience! Thank you!

  6. Lauren

    Lauren

    Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

    We had a really fun trip through the harbor and down the coast for my husband’s Birthday. Captain Andrew was able to find the sweet spot between sharing interesting information and allowing us to enjoy the natural scenery. The kids loved how all the other boats wanted to sail up to ours to yell “Argghhhh!l” and “Ahoy!!!”