Vacation rentals with a kayak in Tisbury

5.0 out of 5 average rating, 99 reviews

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.

Home in Falmouth

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

🌊WATERFRONT LUXURY 🌊 🐕pet friendly! ✨fully renovated! 🐟on spring fed Jenkins Pond w/dock 🚣‍♂️kayaks&stand up paddle-boards! 🚿outdoor shower! 🍽waterfront outdoor dining for 6! 🔥waterfront fire pit area! 📶high speed wifi! 🛏 waterfront Cali king bed nook! 🛏lux linens/bedding 🍽Full kitchen! 📺smart TV in every room! 🪜kids club tv/play loft! 🏖walk 3mins to Jenkins Beach! 🏖15 mins to Falmouth Beaches! 🦞10 mins to Village with tons of restaurants & boutique shopping! *$25/per night pet fee 1 dog only

4.94 out of 5 average rating, 108 reviews

Home in Falmouth

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.

5.0 out of 5 average rating, 103 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

Escape to the beach for a private family reunion or a romantic getaway! Fair Heaven will enchant and accommodate you in luxury. Enjoy the sounds of gentle waves lapping at the private beach and wake up to a day where you may swim off the beach, bike over to the bike trail, or take kayaks out on the warm waters of Buzzard’s Bay. Water shoes are advised on our beach (rocks and shells). A sandy beach is just down the road - permit will be provided. (Certified Massachusetts lodger #C0020560940)

5.0 out of 5 average rating, 93 reviews

Home in Mattapoisett

The Beachfront Estate: 360 Ocean Views, 5700 sqft

Welcome to your exclusive retreat where tranquility meets luxury and sleeps 24 comfortably. This stunning beachfront property offers an unparalleled getaway, ensuring complete seclusion and privacy. Special Features: - Private beach - Stunning 360 degrees ocean and harbor views - 6 bedrooms total: 4 bedrooms have king beds with en suite bathrooms, a bunk room with en suite, and 2nd bunk room / playroom - 6.5 bathrooms - Private road with only two houses - 8 bikes, 6 kayaks, 2 golf club set

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.

4.9 out of 5 average rating, 215 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

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, 219 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!

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, 329 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!

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".

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, 61 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.

4.99 out of 5 average rating, 120 reviews

A serene sunset over a calm body of water reflects vibrant orange and soft blue hues. Lush green grass borders the shore, while silhouettes of distant trees frame the scene. A dock is visible on the left, offering a peaceful spot to enjoy the view.

Home in Wareham

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

5.0 out of 5 average rating, 9 reviews

Home in East Falmouth

Cottage + Guest House | Beach 100 Yards | Sleeps 8

Charming Cape Cod retreat, Bumblebee Cottage, in Falmouth, just 100 yards from private Seacoast Shores beach. This unique property comfortably sleeps 8 across a main cottage and separate guest house, offering a perfect beach getaway with outdoor living, BBQ, and fire pit. Ideal for families, couples, or friends seeking a relaxing escape near kayaking, golfing, and village exploration.