Vacation rentals with a kayak in Tisbury

5 out of 5 average rating, 178 reviews

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

Relaxing Retreat | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

Cottage in South Yarmouth

A view of the waterfront shows a relaxing outdoor seating area featuring a coffee table and comfortable gray sofas. Lush greenery and blooming hydrangeas surround the space, while a clear lake reflects the sky in the background.

5 out of 5 average rating, 240 reviews

SerenityViews | Lakefront | KingBed | Kayaks | FPL

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

4.79 out of 5 average rating, 195 reviews

A calm waterway reflects soft pastel colors during sunrise, with silhouettes of boats anchored in the distance. Gentle grasses line the foreground, and the tranquil landscape is framed by hills on the horizon, offering a serene morning view.

Guest suite in Pocasset

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!

4.99 out of 5 average rating, 197 reviews

The cottage exterior is illuminated by warm lights, showcasing a spacious deck with inviting seating. Lush greenery surrounds the property, with a vibrant purple flowering bush nearby. The serene atmosphere is enhanced by the evening sky, providing a cozy and welcoming retreat.

Cottage in Marion

Little Boho Retreat by the Beach

Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

4.98 out of 5 average rating, 207 reviews

A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

4.94 out of 5 average rating, 249 reviews

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

✅All linens provided & beds made ✅ King bed / Queen / Twin over Full bunk ✅ Direct lake access = natural cold plunge Follow with hot tub recovery! ✅Waterfront hot tub for 6 -Open year round ✅Fully kitchen w/Carrera marble counters ✅Large waterfront dining rm ✅Gas Fireplace in living rm ✅Level backyard to lake ✅Dock for swimming & fishing ✅2 kayaks & 2 SUPs / beach chairs ✅Deck w/sitting & dining area ✅Patio w/seating & gas fire pit ✅Pet fee $30/day ✅W/D Locally managed

4.94 out of 5 average rating, 141 reviews

A view from a window showcases vibrant pink and white flowers in window boxes, framing a serene lake scene. Beyond the flowers, the calm water reflects the gentle colors of the sky, while white Adirondack chairs are positioned on a deck that extends over the pond.

Guesthouse in Plymouth

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Cottage in South Yarmouth

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.

4.92 out of 5 average rating, 504 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

4.94 out of 5 average rating, 159 reviews

A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.

Home in Vineyard Haven

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!

4.91 out of 5 average rating, 197 reviews

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.

Home in Oak Bluffs

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

4.83 out of 5 average rating, 210 reviews

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.

Home in Eastville

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!

5 out of 5 average rating, 334 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

Popular amenities for Tisbury kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.95 out of 5 average rating, 61 reviews

A serene sandy beach stretches along a tranquil lake, with clear blue waters reflecting the sky. Fluffy white clouds drift overhead, and trees line the shoreline in the distance, creating a peaceful natural setting perfect for relaxation or outdoor activities.

Home in Mashpee

Life is Good Rentals in Mashpee

4.88 out of 5 average rating, 169 reviews

The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.

Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

4.99 out of 5 average rating, 90 reviews

A spacious backyard features a circular fire pit surrounded by Adirondack chairs in various colors. In the distance, an inviting in-ground pool is visible, complemented by lush greenery and trees lining the property, creating a serene outdoor setting.

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

4.96 out of 5 average rating, 25 reviews

Home in Mattapoisett

Buzzard Bay Beachfront Getaway

5 out of 5 average rating, 72 reviews

A fire pit area features six sturdy blue Adirondack chairs arranged around a circular stone fire pit, overlooking a serene waterfront view. Lush greenery surrounds the area, with the calm water of Long Pond visible in the background.

Home in South Yarmouth

Sunburst Cottage on Long Pond

4.97 out of 5 average rating, 38 reviews

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.

Home in Oak Bluffs

Spacious 4-Bedroom home with outdoor dining

4.95 out of 5 average rating, 95 reviews

A tranquil scene over a waterfront, featuring a dock extending into the water. Vibrant colors of purple, pink, and orange fill the sky as the sun sets, reflecting softly on the calm surface of the pond.

Home in Falmouth

Private Waterfront Home on Picturesque Pond

4.84 out of 5 average rating, 57 reviews

An outdoor deck area is enclosed by a wooden pergola, featuring climbing greenery and potted flowers. A hot tub is positioned to the left, while comfortable seating is arranged to provide a view of the water. A brick-paved patio complements the setting.

Home in Wareham

Ocean Oasis

Cottage rentals with a kayak

4.94 out of 5 average rating, 124 reviews

The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.

Cottage in Dennis

Compass Rose Cottage ★ Steps to Flax Pond & Trails

4.87 out of 5 average rating, 46 reviews

A private bedroom is viewed through large glass windows, offering a serene lake vista surrounded by trees. A small table with two stools is positioned near the window, while a bedside with a decorative plant enhances the space.

Cottage in Carver

Adorable Lake Front Cottage

4.92 out of 5 average rating, 59 reviews

Cottage in Fairhaven

Seaside Cottage - Steps to Beach/Close to ferry

4.94 out of 5 average rating, 49 reviews

A view from a private deck showcases a scenic waterfront with a sandy beach in the distance. Nearby houses frame the scene, and power lines stretch across the sky, emphasizing the tranquil coastal environment.

Cottage in Onset

Payton's Place is your beach get away.

5 out of 5 average rating, 13 reviews

The kitchen and dining area feature natural wood accents and large windows that provide views of the surrounding greenery. A wooden dining table with woven chairs is positioned near the window, and modern appliances are neatly integrated into the cabinetry, contributing to a bright and airy feel.

Cottage in Plymouth

Cozy, modern cottage on the shore of Long Pond

4.83 out of 5 average rating, 30 reviews

A sandy beach area is viewed, featuring four white Adirondack chairs arranged to overlook a calm lake. Various boats, including kayaks and a sailboat, are visible on the water. Lush green foliage surrounds the scene, enhancing the natural setting.

Cottage in Barnstable

Historic Lakehouse w/PRIVATE beach, boats and SUPs

4.7 out of 5 average rating, 44 reviews

The exterior of the house is viewed from the shore, featuring a grassy area with purple loungers positioned by the water. The house, with its light-coloured siding and multiple windows, overlooks a calm pond surrounded by trees and nearby residences.

Cottage in Onset

The Crab House @ The OBC Beach Resort and Habitat

5 out of 5 average rating, 14 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

Other vacation rentals with a kayak

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, 47 reviews

Cozy immaculate 1 BR+BA near beach!

4.95 out of 5 average rating, 41 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

4.98 out of 5 average rating, 52 reviews

Two white Adirondack chairs are positioned on a sandy beach area by Wequaquet Lake, facing calm waters. A swan glides gracefully in the distance, surrounded by greenery. The serene landscape offers a sense of tranquility, ideal for relaxation.

Home in Barnstable

Private Lake Beach | Spectacular Views & Amenities

5 out of 5 average rating, 31 reviews

A welcoming entrance features a bright yellow front door with decorative wreath, framed by a spacious porch supported by white columns. Lush greenery, including vibrant flowers and shrubs, surrounds the steps, creating an inviting first impression of the home.

Home in Sandwich

7BR/Lakeview/Beach/Oasis Family/Friends/Retreat

4.97 out of 5 average rating, 76 reviews

The exterior view showcases a waterfront property with a spacious backyard. Red Adirondack chairs surround a fire pit, inviting relaxation. Two kayaks are visible on the water, and the serene landscape is complemented by soft evening light reflecting off the water.

Home in Buzzards Bay

Oceanfront | Firepit | Gameroom | Pets | Kayaks

Vacation home in West Tisbury

A charming Cape-style house with a stone façade is nestled among trees. A well-manicured lawn leads to the front, where several outdoor chairs are positioned for relaxation. Sunlight filters through the surrounding foliage, enhancing the serene outdoor setting.

4.91 out of 5 average rating, 11 reviews

Beautiful Family Friendly House with Pool

4.89 out of 5 average rating, 38 reviews

A cozy kitchen area features a rustic wooden island surrounded by two woven bar stools. A vintage white refrigerator and a classic black stove are complemented by open shelving adorned with plants and kitchenware. Bright light streams through a window, enhancing the inviting atmosphere.

Home in West Tisbury

Greenehill~ Up-island 1800's Vineyard farmhouse.