Holiday rentals with a kayak in Edgartown

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.

5 out of 5 average rating, 177 reviews

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.

4.79 out of 5 average rating, 194 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, 195 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, 206 reviews

A serene view of a crystal clear pond is framed by lush trees. The calm water reflects the blue sky and scattered clouds, creating a tranquil atmosphere. A wooden pathway leads to the water's edge, inviting exploration and relaxation.

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

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.

4.94 out of 5 average rating, 249 reviews

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

Tiny home in South Yarmouth

A charming cottage is surrounded by lush green trees and shrubs, set within a spacious yard. A gravel pathway leads to the entrance, while a wooden fence provides privacy. Flower boxes add a touch of color to the exterior near the windows.

4.89 out of 5 average rating, 633 reviews

Romantic 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

4.97 out of 5 average rating, 134 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & high-end sofas in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

4.94 out of 5 average rating, 157 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!

4.79 out of 5 average rating, 102 reviews

A charming cottage is nestled against sandy dunes, featuring a covered porch with seating. The exterior showcases light grey shingles, and a large circular decorative element is centered on one wall. Beach chairs are positioned near the entrance, inviting relaxation with ocean views.

Flat in Harwich Port

Cape Cod Beachfront 2 bedroom Cottage Harwich

This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. Although you'll never feel like you need to leave the cottage because of its enviable location and views, it is close to the quaint Harwich village which boasts art and culture, restaurants and dining, shopping and family-friendly activities. This cottage is great for couples, families (with kids), and groups (up to 5).

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, 332 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 kayak rentals in Edgartown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 13 reviews

The exterior of a designer home is showcased, featuring a spacious backyard that leads to tranquil waters. A hot tub is positioned on a patio surrounded by greenery, while comfortable seating is arranged nearby. The charming architecture complements the serene coastal setting.

Home in West Falmouth

Last Weeks Summer 2026 – Waterfront Available!

A spacious, modern home is set against a vibrant sunset, featuring a large patio area with lounge chairs. Glass doors provide a view of the outdoor hot tub and well-maintained yard, highlighting a welcoming atmosphere for relaxation and enjoyment.

5 out of 5 average rating, 26 reviews

Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!

4.95 out of 5 average rating, 185 reviews

The spacious kitchen features white cabinetry and a modern layout. A central island with seating is complemented by a dining table nearby. Natural light floods the area through sliding glass doors, enhancing the welcoming ambiance.

Home in Yarmouth

Cape Cod Life is Good Rentals

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.

4.97 out of 5 average rating, 39 reviews

Falmouth Summer Fun–Game Barn-Dog Friendly!

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.

5 out of 5 average rating, 72 reviews

Sunburst Cottage on Long Pond

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, 13 reviews

A cozy exterior view of the house features a gravel driveway leading up to a classic Cape Cod cottage. Lush green lawns are complemented by well-maintained gardens and tall trees. The house is set back from the street, with a spacious fenced-in yard enhancing privacy.

Home in Dennis Port

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

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 out of 5 average rating, 78 reviews

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

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

4.92 out of 5 average rating, 59 reviews

Cottage in Fairhaven

Seaside Cottage - Steps to Beach/Close to ferry

4.84 out of 5 average rating, 37 reviews

An aerial view showcases the Cape Cod beach house nestled in a lush green landscape. The surrounding neighborhood features various homes set among trees, with views of nearby water and serene pathways visible in the distance.

Cottage in Hyannis Port

Beach house- walk to ocean + 2 min to Craigville

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

Superhost

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

4.83 out of 5 average rating, 30 reviews

Historic Lakehouse w/PRIVATE beach, boats and SUPs

4.92 out of 5 average rating, 133 reviews

A charming Cape cottage is framed by lush greenery, with sections of neatly mulched garden beds featuring flowering plants. An American flag hangs at the entrance, complemented by a stone walkway leading to the front door. The property is bathed in natural sunlight.

Cottage in Dennis Port

Cape Escape-The Perfect Getaway

4.88 out of 5 average rating, 33 reviews

A view from the dock extends across the calm water of Sand Pond, with lush trees lining the opposite shore. The clear blue sky is reflected in the water, creating a tranquil atmosphere. Two wooden posts stand towards the edge of the dock.

Cottage in Harwich

Lakeside Waterfront House in Harwich: 4+beds, 3bth

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 holiday rentals with a kayak

A serene dock extends over still waters, featuring two lounge chairs positioned for relaxation. Surrounding greenery reflects in the pond, while a sailboat is anchored nearby, adding to the tranquil setting.

5 out of 5 average rating, 13 reviews

Waterfront paradise in Falmouth

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.

Superhost

The private deck features a wooden surface surrounded by lush greenery. A small round table with four chairs and a grill are visible, along with a ceramic pot containing a plant. A lounge chair sits on an area rug with a geometric pattern, enhancing the outdoor space.

Flat in Oak Bluffs

4.79 out of 5 average rating, 217 reviews

Sunny Private studio amazing deck kayaks & kitchen

4.96 out of 5 average rating, 25 reviews

Home in Mattapoisett

Buzzard Bay Beachfront Getaway

5 out of 5 average rating, 65 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

New Seabury Waterfront: Fall At 20% Off!

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.

4.95 out of 5 average rating, 95 reviews

Private Waterfront Home on Picturesque Pond

4.98 out of 5 average rating, 44 reviews

A wooden deck extends over the water, featuring two classic Adirondack chairs facing the harbor. The serene view includes calm water reflecting the sky, with small boats visible in the distance. Tall grass lines the edge, adding a natural touch to the waterfront setting.

Apartment in Nantucket

Spectacular Waterfront Townhouse