Vacation rentals with a kayak in Oak Bluffs

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Top-rated kayak rentals in Oak Bluffs

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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 Marstons Mills

4.91 out of 5 average rating, 177 reviews

Lake Front Stunning Cape Cod Views w Private Beach

Stunning Cape Cod vacation home in Cotuit. Beautiful lake front property. bright, spacious. Private lake beach w fire pit. Large deck with grill overlooking the water. Parking pass to many ocean beaches just a couple minutes away. Nearby beach, ocean beach, trails, shops, restaurants, golf, gym nearby ... Lake is great for swimming, fishing, canoeing and kayaking. Most rooms in the house have a full lake view. (All but one.) Close to Osterville, Centerville, Mashpee, Falmouth and Hyannisport.

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.

Superhost

Guest suite in Pocasset

4.79 out of 5 average rating, 170 reviews

Rustic Beach Cottage

The salty air will instantly wash all your cares away. This rustic charming Cape get away is steps away from a quaint quiet picturesque beach. Simply relax in the comfortable surrounds in this fully furnished 1 bedroom Cottage apartment with all of your basic needs including WiFi, Smart TV, A/C, and a deck complete with gas grill and outdoor furniture offering you plenty of living space inside and out. Close to the bike paths, Cape Cod Canal, great restaurants, hiking, ferry and much much more!

Guest favorite

Home in Tisbury

4.93 out of 5 average rating, 115 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 Mashpee

4.92 out of 5 average rating, 131 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Guest favorite

Cottage in Tisbury

4.98 out of 5 average rating, 45 reviews

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

Superhost

Rental unit in Oak Bluffs

4.81 out of 5 average rating, 176 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

Cottage in East Falmouth

4.93 out of 5 average rating, 158 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

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

Cottage in Falmouth

4.86 out of 5 average rating, 106 reviews

Spectacular Beach front lake house, includes linen

High beamed ceilings with sunny, spacious open kitchen and living room with floor to ceiling windows overlooking the lake. Oversized deck perfect for enjoying the BBQ and view with compfy rocking chairs. Minutes from quaint Falmouth village and Mashpee Commons. Planning a reunion or corporate outing? The house right next door is available for rental! Check out the following listing, "Stunning 4-bedroom Private Fresh Water Beach Front".