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Explore Greetwell

Explore extraordinary experiences in 500+ destinations

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Rentals & Charters

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Questions? We're here to help.Real people, 7 days a week.

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  • 17 Best Places to Kayak in USA: Scenic Routes for 2026
  • Best results for

    Boat Rentals in Oak Bluffs, MA

    Showing 1-15 of 15 results
    21' Boston Whaler Boat Rental in Nantucket
    Up to 8

    21' Boston Whaler Boat Rental in Nantucket

    Rent a 21 ft Boston Whaler for cruising or fishing in Nantucket

    4.2 • 30 reviews
    $1,108/ boat
    20' Center Console Boat Rental in Nantucket

    20' Center Console Boat Rental in Nantucket

    Get out on the water in a Boston Whaler

    4.2 • 30 reviews
    $1,010/ boat
    4-Hour Kayak & Paddleboard Rental in Oak Bluffs

    4-Hour Kayak & Paddleboard Rental in Oak Bluffs

    Rent a kayak or paddle board and explore Oak Bluffs from the water

    4.9 • 162 reviews
    $90/ kayak
    2-Hour Sailboat Rental in Nantucket
    Up to 3

    2-Hour Sailboat Rental in Nantucket

    Take the helm of a Rhodes 19 sailboat

    5.0 • 2 reviews
    $186/ boat
    17' Boat Rental in Martha's Vineyard
    Up to 6

    17' Boat Rental in Martha's Vineyard

    Get out on the water aboard a 17-foot Boston Whaler

    4.5 • 52 reviews
    $347/ boat
    20' Center Console Fishing Boat Rental in Wareham
    Up to 6

    20' Center Console Fishing Boat Rental in Wareham

    Take the helm with fishing-ready features and quiet Suzuki power

    4.3 • 114 reviews
    $365/ boat
    Nantucket 22' Center Console Boat Rental
    Up to 8

    Nantucket 22' Center Console Boat Rental

    Cruise, fish, and relax aboard a spacious 200hp Whaler

    4.2 • 30 reviews
    $1,179/ boat
    17' Boat Rental in Oak Bluffs
    Up to 6

    17' Boat Rental in Oak Bluffs

    Take your group out on a 17-foot Boston Whaler

    4.5 • 52 reviews
    $347/ boat
    20' Walk-Around Boat Rental in Wareham, MA
    Up to 6

    20' Walk-Around Boat Rental in Wareham, MA

    Take the helm with a quiet Suzuki engine and shelter on board

    4.3 • 114 reviews
    $365/ boat
    Nantucket 24' Boston Whaler Boat Rental

    Nantucket 24' Boston Whaler Boat Rental

    Explore Nantucket waters on a spacious 275-hp boat for up to 9 people

    4.2 • 30 reviews
    $1,330/ boat
    Martha's Vineyard 19' Center Console Rental
    Up to 6

    Martha's Vineyard 19' Center Console Rental

    A fishing-ready center console with rod holders and a live well

    4.5 • 52 reviews
    $413/ boat
    22' Mako Boat Rental with Fish Finder in Wareham
    Up to 6

    22' Mako Boat Rental with Fish Finder in Wareham

    Take the helm with GPS and a fish finder on board

    4.3 • 114 reviews
    $393/ boat
    20' Center Console Boat Rental in Nantucket

    20' Center Console Boat Rental in Nantucket

    Take to the water in a Boston Whaler Montauk

    4.2 • 30 reviews
    $954/ boat
    Martha's Vineyard 19' Center Console Boat Rental
    Up to 6

    Martha's Vineyard 19' Center Console Boat Rental

    Take the helm of a 19-foot center console with fishing-ready features

    4.5 • 52 reviews
    $423/ boat
    20' Dual Console Boat Rental in Wareham, MA
    Up to 6

    20' Dual Console Boat Rental in Wareham, MA

    Take the helm for your own time on the water

    4.3 • 114 reviews
    $337/ boat
    Oak Bluffs Things To Do
    Boat RentalsBike Rentals57Kayaking Tours21Sailing18Boat Tours13
    More
    • Guided Hikes13
    • Paddleboarding13
    • Stand Up Paddle Boarding13
    • Fishing Charters7
    • Axe Throwing6
    • Water Skiing5
    • Private Fishing Charters4

    Travel guides for Boat Rentals

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.

    Bus Van and Limo Tours3
  • Yacht Charters3