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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,463 Reviews)

Page 15 of 39932 listings

Hunter 45' - Largest Sailing Yacht in Central Texas, Lake Travis
Sailing in Lakeway · 18 guests

Hunter 45' - Largest Sailing Yacht in Central Texas, Lake Travis

5.0
$299+/hour
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

New
$225/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
Events in Chicago · 13 guests

Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

5.0
$1,190/hour
Lagoon 42´ Catamaran - All Inclusive In Tulum
Sailing in Tulum · 30 guests

Lagoon 42´ Catamaran - All Inclusive In Tulum

5.0
Superowner
$550+/hour
4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun
Sailing in Isla Mujeres · 12 guests

4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun

5.0
Superowner
$221/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

5.0
Superowner
$650+/hour
Instant Book
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
Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks
Sailing in Guanacaste Province · 20 guests

Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks

5.0
$430/hour
Limited Availability
Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/hour
Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests

4.4
Superowner
$157+/hour
EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in La Romana · 150 guests

EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$17/hour
Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Private 37ft Catamaran Charter in Cancún for up to 25 Guests

5.0
Superowner
$157+/hour
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/hour
Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta
Sailing in Marina Vallarta · 8 guests

Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta

New
Superowner
$125/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

5.0
$250/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
Limited Availability
🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina
Sailing in Folly Beach · 6 guests

🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina

5.0
Superowner
$300/hour
Leopard 51 Flybridge Power Catamaran in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 Flybridge Power Catamaran in Tulúm

5.0
Superowner
$607+/hour
Limited Availability
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$725/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
Sailing in Chicago · 12 guests

No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

4.8
$245/hour
55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo

5.0
Superowner
$400+/hour

Sailing Reviews in United States

  1. NE

    Nicole

    🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina

    The absolute highlight of our Charleston trip! Captain Ryan took us on the most beautiful route and brought us to No Name Beach, which honestly felt like our own little private paradise. The weather wasn’t even a picture-perfect sunny day, and it truly didn’t matter one bit. It was one of those days where you just keep thinking, How is this real life, every moment was core memory worthy. Ryan went above and beyond the entire day. He pulled out a huge float for the girls to jump off of, taught us all about the water and the area, and even let the girls help sail the boat. They learned how to blow the conch shell horn to call in the dolphins (which they took VERY seriously 😂 and it actually seemed to work), lounged in the hammock over the water, and basically decided they had become actual sailors. Ryan treated our 9 year-old girls like absolute royalty. They were completely obsessed with him, the boat, the dolphins, the beach…pretty much everything. And they genuinely felt so special, as did us older girls!

  2. FN

    Fadi

    60’ Premier Sailing Yacht in San Diego.

    We had an absolutely amazing experience on our yacht charter! From start to finish, the entire crew made our bachelor trip unforgettable. They were incredibly welcoming, accommodating, and went above and beyond to make sure all of our requests were taken into consideration. Captain Corey and Captain James were outstanding. They were kind, patient, professional, and truly made the celebration even more special. BB was an absolute sweetheart and made everyone feel right at home. Their hospitality and positive energy created an experience we will never forget. Thank you to the entire crew for making our bachelor trip so memorable. We highly recommend this charter to anyone looking for an incredible day on the water. We cannot wait to come back!

  3. EC

    Emily

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Had a group with me and they had a blast. Weather started as misty and then became wonderfully sunny along the way. Hoping to see some sea life but alas none waves were pretty choppy. Boat was wonderful.

  4. BC

    Breck

    Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

    This is by far the best catamaran experience I’ve ever had! The whole trip, the hospitality, the food, the atmosphere, everything about the entire time spent with Clem and crew was truly incredible. I wholeheartedly recommend this experience to everyone I talk to.

  5. DC

    David

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Our group of seven spent a fabulous half day with Captain Rob and Mate Dianna. Couldn't have been happier with the whole experience. Communication was quick and easy. On board, they were super friendly and engaging. The vessel itself was spotless and super comfortable as we hung out on the front "trampoline" area, sailing around the Bay. Thanks for such a fun adventure. We are already talking about a future engagement!

  6. Danika

    Danika

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!