Holiday rentals with a kayak in Oak Bluffs

The exterior of the home is surrounded by a lush green lawn and trees. A spacious deck with umbrellas offers shaded seating areas. The house features multiple levels, blending with the natural landscape, and includes a patio area with lounge chairs.

4.98 out of 5 average rating, 46 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.

LocationOutdoor spacesFamily

4.91 out of 5 average rating, 168 reviews

An open living area features natural wood flooring and soft blue walls. A round dining table sits beside a cozy seating arrangement, creating an inviting space. Large windows enhance natural light, and a modern kitchen area is visible in the background.

Home in Mashpee

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.

Outdoor spacesLocationParks

4.99 out of 5 average rating, 79 reviews

Cottage in Tisbury

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!

LocationOutdoor spacesKitchen

4.93 out of 5 average rating, 187 reviews

Home in Tisbury

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, 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!

LocationOutdoor spacesCheck-in

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.92 out of 5 average rating, 211 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

Outdoor spacesLocationIndoor spaces

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

4.83 out of 5 average rating, 216 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. Ask the host about ferry reservations if they appear to be sold out!

LocationValueView

Superhost

The dining area features a round wooden table surrounded by four black and natural chairs, with a tasteful floral arrangement at the center. Large glass doors provide a view of the ocean, and a cozy living space with a gas fireplace is visible in the background.

Home in Pocasset

4.83 out of 5 average rating, 40 reviews

Pocasset Private Beach Family Retreat/firepit

Nestled in an exclusive community with a private association beach, this captivating new construction offers unparalleled sophistication and breathtaking water views from every room. Step inside and experience the exquisite interior, adorned with custom finishes and smart home features. The fabulous upscale kitchen, complete with top-of-the-line appliances, flows seamlessly into the dining and living spaces, which feature soaring ceilings and a cozy gas fireplace.

LocationOutdoor spacesView

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.93 out of 5 average rating, 316 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

ValueLocationWalkability

5 out of 5 average rating, 14 reviews

Home in Barnstable

Private Waterfront Escape | Kayaks + Firepit

🌊 Waterfront Cape Cod Escape | Beach Pass Included Wake up to ocean views, walk to the shoreline, and spend your days exploring Cape Cod’s best beaches—with your included Barnstable Beach Pass. Unwind on your private patio, gather around the firepit at night, and enjoy a peaceful coastal retreat designed for comfort and connection. Perfect for families, couples, and small groups looking for a relaxing, high-quality Cape Cod stay.

Outdoor spacesLocationBackyard

4.95 out of 5 average rating, 43 reviews

The kitchen features sleek countertops, stainless steel appliances, and a unique table supported by a natural wood base. Large windows provide ample natural light, illuminating the space. Cabinets offer storage solutions, while the stove and sink are conveniently positioned for ease of use.

Apartment in Edgartown

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

LocationOutdoor spacesAir conditioning

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.

4.98 out of 5 average rating, 54 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.

LocationOutdoor spacesAccuracy