Holiday rentals with a kayak in Oak Bluffs

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Top-rated rentals with kayak in Oak Bluffs

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite

Home in Barnstable

4.91 out of 5 average rating, 175 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.

8–15 Mar

$932 SGD per night

Guest favourite

Home in Oak Bluffs

5.0 out of 5 average rating, 24 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.

24–31 Dec

$1,244 SGD per night

Guest favourite

Home in Tisbury

4.92 out of 5 average rating, 89 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!

6–13 Oct

$792 SGD per night

Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 179 reviews

Waterview, Private, Walk to Beach, Mile to Town

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. Please view our entire listing and reviews for more about our unique property.

23–30 May

$655 SGD per night

Superhost

Home in Mashpee

4.9 out of 5 average rating, 114 reviews

Johns Pond; private BEACH, 2 Kayaks & Fire Pit

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 firepit and dining area.

15–22 Dec

$498 SGD per night

Guest favourite

Townhouse in Edgartown

4.97 out of 5 average rating, 33 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. PLEASE NOTE: In high season (late June to Labor Day,) we can only accept Saturday to Saturday requests.

18–25 Jun

$615 SGD per night

Guest favourite

Flat in Edgartown

4.92 out of 5 average rating, 24 reviews

Katama Loft

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.

20–27 Oct

$398 SGD per night

Guest favourite

Cottage in Tisbury

4.97 out of 5 average rating, 33 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!

1–8 Dec

$1,543 SGD per night

Superhost

Flat in Oak Bluffs

4.8 out of 5 average rating, 139 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.

18–25 Jan

$293 SGD per night

Superhost

Home in Oak Bluffs

4.91 out of 5 average rating, 126 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

26 Feb – 5 Mar

$1,089 SGD per night

Guest favourite

Cottage in Falmouth

4.93 out of 5 average rating, 136 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.

7–14 Apr

$251 SGD per night

Superhost

Guest house in Bourne

4.78 out of 5 average rating, 123 reviews

Rustic Carriage House by the Sea

This is an authentic small old Cape Cod rustic carriage House. Which is charming, antique and unique. It is in a beautiful one-of-a-kind location. Loaded with cozy fun. A great getaway any time of the year! The Carriage house is walking distance away from beautiful Hens cove and is near many activities, Bike paths, the canal, the ferry, hiking, fishing, and many restaurants. Great for pet friendly Families, a couple of couples, friends that want to stay together, and bigger groups.

28 Oct – 4 Nov

$203 SGD per night