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Oak Bluffs, Massachusetts Boat Rentals - 2023

24 listings
Come Sail the Vineyard on our well cared for 34' Beneteau!
Sailing in Oak Bluffs · 6 guests

Come Sail the Vineyard on our well cared for 34' Beneteau!

New
$200hour
Sea Ray 280 Motor Yacht Rental in Oak Bluffs, Massachusetts
Events in Oak Bluffs · 6 guests

Sea Ray 280 Motor Yacht Rental in Oak Bluffs, Massachusetts

New
$550hour
60' Cruising Monohull Ketch in Vineyard Haven, MA
Sailing in Tisbury · 12 guests

60' Cruising Monohull Ketch in Vineyard Haven, MA

5.0
$200-275hour
28ft Whitewater Center Console Rental in Mashpee, Massachusetts
Powerboats in Mashpee · 6 guests

28ft Whitewater Center Console Rental in Mashpee, Massachusetts

5.0
$300hour
8 Person Center Console Rental in Osterville Massachusetts
Powerboats in Barnstable · 8 guests

8 Person Center Console Rental in Osterville Massachusetts

5.0
$225hour
27' Blackfin Center Console in Osterville & Barnstable, Cape Cod
Powerboats in Barnstable · 6 guests

27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

5.0
$350hour
Yamaha 195S Wakeboat in Sandwich
Powerboats in Sandwich · 8 guests

Yamaha 195S Wakeboat in Sandwich

5.0
$625day
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

New
$150hour
Half Day 26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod
Powerboats in Barnstable · 12 guests

Half Day 26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod

New
$250hour
Half Day Rental | 22ft Aqua Patio Pontoon Boat in Hyannis Harbor - Cape Cod
Powerboats in Barnstable · 10 guests

Half Day Rental | 22ft Aqua Patio Pontoon Boat in Hyannis Harbor - Cape Cod

New
$174hour
Full Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

Full Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690day
Half Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Half Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

5.0
$119hour
Full Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

Full Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$775day
Half Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

Half Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$144hour
Full Day Rental | 22' Aqua Patio Pontoon Boat in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 10 guests

Full Day Rental | 22' Aqua Patio Pontoon Boat in Hyannis Harbor, Massachusetts - Cape Cod

New
$895day
Half Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

Half Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$119hour
Half Day Rental | 17′ Montauk Center Console Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Half Day Rental | 17′ Montauk Center Console Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$99hour
Half Day Rental | 16ft Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 6 guests

Half Day Rental | 16ft Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$99hour
Full Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Full Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690day
Full Day Rental | 26’ Regulator Center Console  in Hyannis, Massachusetts - Cape Cod
Powerboats in Barnstable · 12 guests

Full Day Rental | 26’ Regulator Center Console in Hyannis, Massachusetts - Cape Cod

New
$1,595day
Half Day Rental | 22' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

Half Day Rental | 22' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$174hour
Sea Ray 380 Sundancer Cape and Islands
Events in Barnstable · 12 guests

Sea Ray 380 Sundancer Cape and Islands

5.0
$550hour
Sunset Charter for 6 persons - Private 42 trawler- Hyannis Ma. Starts at 6pm
Events in Barnstable · 6 guests

Sunset Charter for 6 persons - Private 42 trawler- Hyannis Ma. Starts at 6pm

5.0
$300hour
Cruise Martha's Vineyard and Cape Cod on a Captained 30ft Back Cove
Powerboats in Wareham · 6 guests

Cruise Martha's Vineyard and Cape Cod on a Captained 30ft Back Cove

New
$298hour

Oak Bluffs Reviews

  1. KN
    Kelley
    8 Person Center Console Rental in Osterville Massachusetts

    We had such a fun time with Captain Bill! This was the perfect outing for our group of 7. Captain Bill had great music and a very clean boat. Awesome time overall. We would recommend Captain Bill to anyone looking to have a fantastic day on the water.

  2. Samantha
    Samantha
    27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

    Captain Mac was awesome. We did a quick charter on his black fin out of Falmouth. His boat was beautiful and he got us super safely to Hadley’s harbor for a nice swim. It was a great experience for our group and I would highly recommend!

  3. Nicholas
    Nicholas
    27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

    Mike is the consummate professional and an absolute stud. He builds rock walls with his bare hands and his equipment is top notch. Picks you up, drops you off, on time and had the best recommendations on what to do based on our preferences. This experience was absolutely amazing and was one of the best days of our lives. We will absolutely be using Mike again on our next and future high seas adventures.

  4. JB
    Jacklyn
    Yamaha 195S Wakeboat in Sandwich

    Everything about Caleb and his boat was awesome! He was so accommodating and had great communication. He had great recommendations that made for a very enjoyable day with my family

  5. SD
    Stewart
    60' Cruising Monohull Ketch in Vineyard Haven, MA

    Sequoia and his crew were very accommodating. My wife had been in an accident and was wearing a cast. They made sure they used the utmost care in getting her on and off the boat. The weather was beautiful and we toured the harbor and they gave us a history of some of the tall ships and wooden boat yard. The recommendation for lunch at the Black Dog was great. Fun time _/)

  6. Barbara
    Barbara
    28ft Whitewater Center Console Rental in Mashpee, Massachusetts

    We were very impressed with Capt Mike! His communication was impeccable! Incredibly responsive! His boat was very clean! He was very kind and understanding. He took us on a lovely tour out of Mashpee! We couldn't have asked for a better experience. Would HIGHLY recommend hiring Capt Mike for your charter. Seriously an amazing afternoon.