Vacation rentals with a kayak in Dukes County

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Top-rated kayak rentals in Dukes County

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Superhost

Home in Falmouth

Modern Waterfront Home & Exclusive Quissett Beach

Escape to a one-of-a-kind architectural haven nestled between downtown Falmouth and Woods Hole. Cygnus House blends mid-century modern elegance with zen-inspired tranquility, perched directly on the freshwater Oyster Pond and offering exclusive Quissett Beach (ocean) access, curated interiors and panoramic views. Whether you’re savoring a moment of calm by the water, soaking in the Japanese Hinoki tub, or exploring local culture, Cygnus House is your Cape Cod sanctuary for reflection and style.

Guest favorite

Home in Tisbury

4.94 out of 5 average rating, 139 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!

Superhost

Apartment in Oak Bluffs

4.79 out of 5 average rating, 204 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, 183 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 West Tisbury

4.87 out of 5 average rating, 30 reviews

Greenehill~ Up-island 1800's Vineyard farmhouse.

Enjoy the laid-back up-island charm of this 1800's rustic farmhouse. True Vineyard vibes with this cozy cottage located in the heart of West Tisbury. Next door to NTFM which offers everything from fresh morning croissants to delicious cheeses. Cronig's Grocery store, State Road Restaurant, Poly Hill Arboretum, WT farmers market, nature trails are all walking distance. Walk-on beach pass to Lamberts cove. All that up-island has to offer. Slow down this summer at Greenehill @greenehillmv

Guest favorite

Home in Falmouth

4.91 out of 5 average rating, 22 reviews

Falmouth Heights spacious luxury for groups

Amazing location Falmouth Heights for two families ideal for group of wedding guests. Two Houses in One Property. 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 with your group.

Guest favorite

Guest suite in Oak Bluffs

4.79 out of 5 average rating, 48 reviews

Tree Top Suite Get-Away

Our beautiful suite has a private entrance, is a 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 private full bath, kitchenette and outside deck surrounded by 70 foot trees. Internet and TV for streaming included. You’ll love our suite because of the location, the light, the coziness and the homey feel. It is a wonderful space couples, friends or a self love retreat.

Guest favorite

Home in Oak Bluffs

4.88 out of 5 average rating, 16 reviews

Bucolic, modern home near town, beaches

This stunning 4 BR home, a few miles from Oak Bluffs, offers both elegance and comfort. A short garden path leads to a PRIVATE BEACH, creating an ideal retreat. Sunlight fills the space, including a chef’s kitchen. Perfect for families or couples seeking a getaway. Escape the everyday. Relax in this serene, magical spot. This listing is new due to a change in management. We've rented this home since 2006 with many 5-star reviews and repeat guests.

Guest favorite

Apartment in Edgartown

4.94 out of 5 average rating, 34 reviews

Katama Loft

Very cute clean apt with private outdoor space. 1.5 miles to either downtown or beach. 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. Thoughtful touches throughout and your comfort always in mind

Top guest favorite

Home in Oak Bluffs

4.97 out of 5 average rating, 35 reviews

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

Top guest favorite

Townhouse in Edgartown

4.98 out of 5 average rating, 49 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

4.87 out of 5 average rating, 71 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.