Holiday rentals with a kayak in Dukes County

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.

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

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

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.

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

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.

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.

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.

Beautiful Edgartown Colonial with heated pool.

Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.