Vacation rentals with a kayak in Edgartown

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.

LocationValueBathroom

4.94 out of 5 average rating, 104 reviews

Private Waterfront Home on Picturesque Pond

Welcome to this bright and airy waterfront home on beautiful Mares Pond. This tranquil property is the perfect place to spend some time away in a peaceful setting, and is set up wonderfully for multiple families. The house is perfectly located to enjoy all that Falmouth has to offer. Just 10 minutes to Falmouth ocean beaches, Falmouth Village shopping and restaurants. Drive or take the trolley to Woods Hole in less than 20 minutes, or hop on the ferry to Martha's Vineyard just down the road.

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!

LocationValueWalkability

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 spacesLocationHospitality

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!

ValueLocationDecor

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!

LocationOutdoor spacesHiking

4.87 out of 5 average rating, 115 reviews

Large floor-to-ceiling windows frame a view of the lake, inviting natural light into the space. The open-concept living area features a comfortable seating arrangement, a dining table, and decorative elements such as floral centerpieces. Wooden beams highlight the high ceilings, enhancing the spacious feel.

Cottage in Falmouth

Spectacular Beach- front home, 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".

LocationOutdoor spacesKitchen

4.95 out of 5 average rating, 42 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 spacesGetting around

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, 53 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.

Outdoor spacesLocationBathroom

4.98 out of 5 average rating, 64 reviews

A large deck is furnished with a round table surrounded by six green chairs. An umbrella provides shade over the table. A lounge chair rests nearby, and a grill is positioned to the side. Glass doors lead into the inviting interior space.

Townhouse in Oak Bluffs

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.

ValueLocationQuiet

4.96 out of 5 average rating, 28 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

September: FIVE (5) night minimum stay. Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool closes: Columbus Day week

LocationOutdoor spacesQuiet

4.94 out of 5 average rating, 227 reviews

A bright living area features wooden beams across the ceiling and light walls. A comfortable couch with decorative pillows faces a coffee table stacked with magazines. Two lamps provide ambient lighting, while sunlight enters through multiple windows, creating a welcoming environment.

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

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.

LocationValueLong stay

Popular amenities for Edgartown kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 6 reviews

Dreamy Falmouth Retreat Walk to Beach + Big Yard!

LocationOutdoor spacesFamily

The exterior of a traditional Cape Cod home is shown at dusk, featuring large windows that illuminate the cozy living area. Adirondack chairs are positioned on the green lawn, surrounded by bare trees. A separate structure is visible, adding to the charm of the backyard.

4.98 out of 5 average rating, 54 reviews

Falmouth Summer Fun–Game Barn-Dog Friendly!

Outdoor spacesLocationBeach

A sleeping nook features a spacious bed adorned with a colorful floral comforter. Wall decor spells out 'COZY' in decorative letters. A mounted smart TV is positioned above the bed, and natural light illuminates the room through nearby windows.

5.0 out of 5 average rating, 95 reviews

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

ValueLocationSleep quality

5.0 out of 5 average rating, 100 reviews

A serene coastal view showcases calm waters meeting a rocky shoreline, with gently lapping waves in the distance. Lush greenery and coastal plants frame the foreground, creating a natural border to the beach scene under a clear blue sky.

Home in Fairhaven

Fair Heaven, your West Island beachfront home

LocationOutdoor spacesCondition

A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.

4.97 out of 5 average rating, 34 reviews

Renovated ranch with pool access

Outdoor spacesLocationQuiet

The two-story home features a sleek white exterior with black accents. A set of wide steps leads to the front door, framed by large windows. A well-maintained lawn and driveway provide access, while trees gently surround the property, ensuring a sense of privacy.

5.0 out of 5 average rating, 27 reviews

Beautiful home! Clubhouse pool, tennis, basketball

Outdoor spacesLocationIndoor spaces

The exterior of the ranch-style home features a spacious deck with seating and a hammock, surrounded by landscaping. Kayaks are available below the deck, and large windows provide ample natural light. The property is set within a green, tree-lined area, enhancing the outdoor appeal.

5.0 out of 5 average rating, 28 reviews

Waterfront Home w/Dock, Deck, Central A/C & Kayaks

Outdoor spacesValueAmenities

A sandy shoreline leads to calm waters, with a wooden dock extending out towards the horizon. Lush greenery is visible in the distance, framed by gentle waves reflecting the clear blue sky. This serene setting offers a peaceful atmosphere for relaxation.

4.89 out of 5 average rating, 92 reviews

Private Beach Access, Kayaks, Outdoor Shower+Bikes

Outdoor spacesLocationAmenities

Cottage rentals with a kayak

4.89 out of 5 average rating, 18 reviews

Cottage in Chilmark

Marthas Vineyard Cottage - Path To Menemsha Beach

Outdoor spacesLocationQuiet

5.0 out of 5 average rating, 12 reviews

The cottage exterior is framed by lush greenery and stone landscaping, featuring a welcoming porch with rocking chairs. Colorful flower pots and pumpkins are placed around, while a serene view of the water is visible in the background.

Cottage in Oak Bluffs

The WestLake

Outdoor spacesLocationBeach

5.0 out of 5 average rating, 18 reviews

An aerial view displays a charming beach house surrounded by lush greenery and an expansive lawn. The structure features a sloped roof and a welcoming set of stairs leading to the entrance. The bay glimmers in the background, showcasing tranquil waters and a clear sky.

Cottage in Fairhaven

“Valhalla” on West Island

LocationOutdoor spacesCheck-in

4.91 out of 5 average rating, 45 reviews

The exterior of the cedar-shingled cottage is shown amidst a naturally landscaped area, featuring trees that provide shade. A wooden deck entrance leads to the front door, with flowering plants adding color. The water is visible in the background, enhancing the serene atmosphere.

Cottage in Mashpee

2-Bdrm Beach Cottage

Outdoor spacesValueBathroom

5.0 out of 5 average rating, 23 reviews

A stone pathway is bordered by lush greenery and blooming hydrangeas, leading up to a light-colored cottage entrance. The pathway is flanked by vibrant blue flowers, creating a welcoming approach to the front door.

Cottage in Woods Hole

Cheerful 4 bedroom cottage in Woods Hole!

LocationOutdoor spacesKitchen

4.91 out of 5 average rating, 11 reviews

Cottage in East Falmouth

Private Beach Cottage with Kayak

Outdoor spacesLocationCondition

Superhost

Cottage in Chilmark

4.92 out of 5 average rating, 12 reviews

Pilot House- The Famous Menemsha Inn Cottage

ValueLocationNearby

Other vacation rentals with a kayak

Superhost

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Apartment in Aquinnah

4.6 out of 5 average rating, 35 reviews

Quiet & Serene in Aquinnah

ValueLocationHospitality

5.0 out of 5 average rating, 69 reviews

A spacious deck is shown, featuring several white outdoor tables and chairs, ideal for dining or relaxation. Lush greenery surrounds the area, and a grill is positioned at one end. The tranquil water of Ockway Bay reflects the sky, creating a serene atmosphere.

Home in New Seabury

Waterfront New Seabury Waterfront House!

LocationOutdoor spacesGrill

Guest suite in New Seabury

A serene pond is enhanced by a gently cascading waterfall, illuminated by soft lights. Natural stones form the water feature, surrounded by lush greenery and subtle plant life, creating a tranquil setting for relaxation.

4.98 out of 5 average rating, 55 reviews

Cozy immaculate 1 BR+BA near beach!

LocationValueGetting around

4.86 out of 5 average rating, 71 reviews

An open dining area features a long wooden table with seating for eight, surrounded by neutral-toned chairs. Large windows provide natural light, while textured rugs complement the hardwood floor. A living space with a sofa and a mounted television is visible in the background.

Home in New Seabury

Modern & spacious New Seabury house w/ pond access

LocationValueBackyard

A two-story blue house is surrounded by lush green grass and neatly trimmed shrubs. The entrance features a brick path leading to the door, flanked by decorative flower pots. Windows framed in white reflect natural light, adding to the home’s welcoming appearance.

4.86 out of 5 average rating, 35 reviews

5BR Cape House - Steps to the Water

Outdoor spacesLocationAmenities

4.96 out of 5 average rating, 46 reviews

A spacious living area features a sectional sofa adorned with decorative pillows, positioned near a fireplace with a large wall-mounted TV above it. The room’s blue walls complement a dining space visible in the background, showcasing a round dining table surrounded by upholstered chairs.

Home in New Seabury

Near Beach|Shopping/Dining|Renovated|King Bed

LocationOutdoor spacesWifi

5.0 out of 5 average rating, 11 reviews

Home in Fairhaven

Stunning Sunset Views, Steps to Water

LocationDecorComfort