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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,459 Reviews)

Page 22 of 39930 listings

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2026
$75/hour
Rent our 25ft Sailboat in Kemah, Texas
Sailing in Seabrook · 4 guests

Rent our 25ft Sailboat in Kemah, Texas

5.0
$54/hour
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350/hour
30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter
Sailing in Cancún · 30 guests

30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter

New
$540/hour
Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!
Sailing in Herradura · 35 guests

Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!

5.0
$500/hour
Private 60ft Power Catamaran in Cabo San Lucas – Up to 80 Guests
Sailing in Marina · 80 guests

Private 60ft Power Catamaran in Cabo San Lucas – Up to 80 Guests

New
$1,000/hour
Instant Book
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450/hour
⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta
Sailing in Marina Vallarta · 16 guests

⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta

4.0
$480+/hour
Crewed Charter 42' Lagoon Sailing Catamaran from Playa del Carmen
Sailing in Playa del Carmen · 20 guests

Crewed Charter 42' Lagoon Sailing Catamaran from Playa del Carmen

5.0
$750/hour
Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami
Events in Miami · 14 guests

Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

New
$350/hour
Sail from Delray Beach to Lake Boca
Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0
Superowner
$125+/hour
Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience
Sailing in Los Melones · 35 guests

Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience

New
$850/hour
Instant Book
40' Catamaran - Sail away
Sailing in Marina del Rey · 6 guests

40' Catamaran - Sail away

5.0
$400/hour
45ft  Luxury Catamaran Private Charter / Capacity 38 people
Sailing in Cancún · 40 guests

45ft Luxury Catamaran Private Charter / Capacity 38 people

New
Superowner
$572+/hour
45' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 30 guests

45' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$393+/hour
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$950/day
Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston

New
$250/hour
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90+/hour
Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views
Powerboats in Folly Beach · 6 guests

Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views

New
Superowner
$150/hour
42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$150+/hour
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

5.0
$550/hour
45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay
Sailing in San Diego · 6 guests

45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

5.0
$550+/hour
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2026
$75/hour
Luxury 52 Catamaran With  AC - Price include 2 People
Sailing in Guna Yala Comarca · 8 guests

Luxury 52 Catamaran With AC - Price include 2 People

5.0
$2,700/day

Sailing Reviews in United States

  1. DF

    Dina

    Rent our 25ft Sailboat in Kemah, Texas

    Loved the sailing experience on the 25 foot sailboat. Eventhough it was an old sailboat form the 80's, David, our captain, was in control of every detail. He is a great captain. He is very paused and confident and easy to get along with. Recommend David with closed eyes. Lucy and the rest of the gals at the office are great people.

  2. DP

    Dawn

    Luxury 52 Catamaran With AC - Price include 2 People

    ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

  3. AA

    Adam

    45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

    What can I say except a big thank you for the best experience I’ve had before! It’s been an adventure holiday and for me personally, an awakening. You gave it your all for me and it's been totally great. Your new friend, Adam.

  4. RC

    Ryan

    Sunset Cruise in Myrtle Beach, South Carolina

    Great trip! The captain was terrific! Most of the time is spent going to and from the open ocean, but it is a scenic voyage. Fair price. Boat is in good-fair condition. We grabbed take-out at the marina before pushing off.

  5. MS

    Michelle

    Catalina 27 Sailboat Rental in Olga, Washington

    Lots to learn of you're new at sailing. Great teacher. Guess over it until you get it. Did a wonderful job explaining everything. The who what when where and why's. Also gave us a great dinner ideas.

  6. WL

    William

    Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!

    I rented the catamaran and it’s was good. We saw whales, baby sea turtles and more. The captain ( Elias ) was fantastic. The deck hand was also great. Boat was also great.