Vacation rentals with a kayak in Dukes County

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Top-rated kayak rentals in Dukes County

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Guest favorite

Guest suite in Oak Bluffs

4.81 out of 5 average rating, 27 reviews

Sweet Suite Close to Beach and Town

Our beautiful suite has a private entrance, is a short walk down an old fashioned dirt road to a private beach and also right off the bike path into the town of Oak Bluffs. The room is perfect for two with a kitchenette, private full bath, brand new outdoor shower & patio surrounded by 70 foot trees. Internet and TV for streaming. You’ll love our suite because of the location, the light, the coziness and the homey feel. It is a wonderful space for couples, close friends or a self love retreat.

Guest favorite

Home in Oak Bluffs

5 out of 5 average rating, 32 reviews

Spacious 4-Bedroom home with outdoor dining

The main floor greets you with an expansive living room, 65" television and pool table. The kitchen has granite countertops with a bar that seats four and large dining area with sliders to outdoor dining. The home includes the use of 2 kayaks that are housed at the association dock on Sengekontacket Pond, tennis/pickleball courts. It is located right off the bike path and includes the use of 2 bikes. Comfortably sleeps 8-10 in 4 bedrooms plus a Murphy bed. The is also a garage for storage.

Guest favorite

Home in Tisbury

4.93 out of 5 average rating, 114 reviews

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, garden and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Guest favorite

Home in Falmouth

4.95 out of 5 average rating, 20 reviews

Falmouth Heights spacious luxury for groups

Looking for Falmouth Heights? Are you two families? Group of wedding guests? Two Houses for the price of One! Getaways and wedding parties. WALK everywhere! Sleeps 8-10 people comfortably with room for up to 13. Easy Heights Beach walk or Island Queen ferry to Martha's Vineyard. >1 mile to Village shops, Inner Harbor restaurants, and groceries. Head to the beach for the day or take the kayaks for a paddle. When the sun is setting grill out in the expansive back yard while enjoying the patio.

Guest favorite

Rental unit in Edgartown

4.94 out of 5 average rating, 33 reviews

Katama Loft Bicycles included!

Newly remolded apt 2 miles to either downtown or beach with bike path across the street! Restaurants and general store within a half mile. One bedroom ,living room area, kitchen with stove, microwave, and convection oven and cookware. Grill, outdoor dining, smart tv, wifi, beach gear, laundry, and more! Bikes and kayaks available on request. Apartment is just newly renovated August 2022 (was rented year round for past 7 years). Thoughtful touches throughout and your comfort always in mind.

Guest favorite

Home in Falmouth

4.9 out of 5 average rating, 62 reviews

Stroll to Beach! Dog Friendly Sunny Cape House

Everything new & updated in this Falmouth beach house with a relaxed West Coast-meets-East vibe. Located on a quiet street in the coveted Teaticket neighborhood, load up the beach wagon and stroll to popular Bristol Beach or launch the kayak in Little Pond just a few houses down. Rinse off in the outdoor shower upon your return & relax with the pup in the fully fenced backyard. 10 min walk to Bristol Beach 15 min walk to Falmouth Heights Beach 1.7 mi Island Queen Ferry Learn more below!

Superhost

Rental unit in Oak Bluffs

4.81 out of 5 average rating, 175 reviews

Sunny Private studio amazing deck kayaks & kitchen

Discover a cozy studio apartment designed for two, complete with its own entrance and a private deck where you can unwind during your island getaway. Enjoy the convenience of a fully equipped kitchen, beach chairs, a beach bag/cooler, and beach towels, all provided for your comfort. Located just a mile away from town and a short 12-minute bike ride to the beach, this spot offers the perfect blend of easy access to Oak Bluffs' restaurants, outdoor activities, and a tranquil neighborhood.

Guest favorite

Home in Oak Bluffs

4.92 out of 5 average rating, 166 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Guest favorite

Home in Oak Bluffs

4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

Ask the host about ferry reservations if they appear to be sold out! Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing.

Guest favorite

Guest suite in West Tisbury

4.97 out of 5 average rating, 75 reviews

Quiet West Tisbury 2 BDR Suite

We are inviting you to stay in the two bedroom, full bath 1st floor wing of our home which has its own private entrance. On 3 acres in a quiet area in the center of the island, the house is in a wooded area that leads to numerous island trails. The town of West Tisbury is 1.5 miles away with a bakery, general store, library and church. Included with your stay is access to the town’s private beach, Lamberts Cove which is an island favorite and only 2 miles away.

Guest favorite

Townhouse in Edgartown

4.98 out of 5 average rating, 41 reviews

Surf and Turf Townhouse

Cozy 2 bdr, 1.5 bath townhouse perfect for a family of four looking for an action-packed Martha's Vineyard vacation. We are located right between Oak Bluffs and Edgartown offering easy access to all down-island towns and bike paths. The development provides access to dock on Sengekontacket (where you'll find our two kayaks) a freshwater pond, and tennis/pickle ball courts for you to enjoy.

Superhost

Home in Falmouth

4.93 out of 5 average rating, 44 reviews

Cozy Pet Friendly Falmouth Beach House

Welcome to our cozy East Falmouth beach house located down the road from beautiful Cape Cod Beaches! There are many local local amenities to enjoy during your stay including restaurants, bars, beaches, mini golf, golfing, a winery, Woods Hole, boating, fishing, and much more! So bring the whole family and getaway with a group of friends.