Holiday rentals with a kayak in Falmouth

4.83 out of 5 average rating, 127 reviews

Cottage in Harwich Port

2BR Directly on Pleasant Beach – 30 Steps to Ocean

You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. 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. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.

Outdoor spacesLocationBeach

5.0 out of 5 average rating, 6 reviews

Home in East Falmouth

Dreamy Falmouth Retreat Walk to Beach + Big Yard!

Experience classic Cape Cod living at this newly renovated home in the Shorewood Beach neighborhood of East Falmouth. Walk to a private association dock and enjoy access to three private beaches on Great Pond - perfect for kayaking, swimming, or relaxing by the water. This 2 bedroom, 1 bath home features a bright open layout, modern kitchen, gas fireplace, & bonus room. Outside, enjoy a fenced in yard and patio w/ fire pit, outdoor shower, & grill. Close to beaches, dining, & downtown Falmouth!

LocationOutdoor spacesQuiet

4.96 out of 5 average rating, 164 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 & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen 🛁New Bathroom 🕊️Relax out back in peace & privacy or go explore! 📍 Centrally located ❌NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

ValueOutdoor spacesIndoor spaces

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.

LocationValueShared spaces

4.99 out of 5 average rating, 100 reviews

Home in Sandwich

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

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

Outdoor spacesValueCheck-in

4.89 out of 5 average rating, 668 reviews

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.

Tiny home in Yarmouth

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

LocationOutdoor spacesAccess

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.

4.91 out of 5 average rating, 167 reviews

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 spacesLocationBarbecue

5.0 out of 5 average rating, 130 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries

ValueLocationHospitality

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.

ValueOutdoor spacesQuiet

4.93 out of 5 average rating, 316 reviews

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.

Home in Oak Bluffs

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!

ValueOutdoor spacesBathroom

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".

Outdoor spacesValueSleep quality

4.99 out of 5 average rating, 113 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.

ValueLocationHospitality

Popular amenities for Falmouth kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.99 out of 5 average rating, 330 reviews

A private waterfront deck offers a serene view of Flax Pond, surrounded by lush greenery. Adirondack chairs are positioned for relaxation, providing a perfect spot to enjoy the tranquil waters and natural surroundings.

Home in Dennis

Stunning Waterfront with Serene Sunrise Views!

LocationOutdoor spacesView

5.0 out of 5 average rating, 363 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

ValueLocationCleanliness

4.97 out of 5 average rating, 119 reviews

A charming living room features a comfortable sofa with blue and white patterns, situated beside a warm gas fireplace. Sunlight filters through windows, illuminating a coffee table with a tray and snacks. Bookshelves adorned with decorative items line the walls, enhancing the cozy ambiance.

Home in Harwich Port

Pebbles-romantic cottage for two!

LocationOutdoor spacesAmenities

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

ValueLocationIndoor spaces

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!

ValueLocationBeach

4.97 out of 5 average rating, 34 reviews

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.

Home in East Falmouth

Renovated ranch with pool access

LocationOutdoor spacesQuiet

Superhost

5.0 out of 5 average rating, 4 reviews

Modern Waterfront Home & Exclusive Quissett Beach

LocationFamilyHiking

5.0 out of 5 average rating, 27 reviews

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.

Home in East Falmouth

Beautiful home! Clubhouse pool, tennis, basketball

LocationOutdoor spacesComfort

Cottages with a kayak

5.0 out of 5 average rating, 252 reviews

A serene waterfront view showcases a tranquil pond surrounded by lush greenery. Two kayaks are visible on the grassy area, while the deck features a wooden table with white chairs, inviting relaxation and outdoor dining.

Cottage in Yarmouth

SerenityViews | Waterfront | King Bed | Kayaks SUP

LocationValueHiking

4.84 out of 5 average rating, 283 reviews

A serene view of a clear, spring-fed pond is visible, edged by lush greenery. A wooden dock extends into the water, inviting activities such as swimming or kayaking. Gentle waves ripple on the surface, reflecting the surrounding trees under a clear blue sky.

Cottage in Wareham

Cozy Cottage on a Private Pond

ValueOutdoor spacesHeating

4.98 out of 5 average rating, 241 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 ★

Outdoor spacesValueComfort

5.0 out of 5 average rating, 238 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

LocationValueQuiet

4.96 out of 5 average rating, 275 reviews

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

The Breeze Overlooking Minister's Pond

Outdoor spacesLocationCheck-in

4.95 out of 5 average rating, 132 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

Outdoor spacesLocationPets

4.93 out of 5 average rating, 138 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

Outdoor spacesValueFamily

4.98 out of 5 average rating, 65 reviews

A view from the interior of the cottage showcases large windows framing the serene water scene outside. A wooden dining table with chairs is visible, along with a desk area that faces the water. Exposed beams line the ceiling, enhancing the rustic design.

Cottage in Barnstable

Serenity Point Waterfront (Now Booking for Fall)

Outdoor spacesLocationDecor

Other holiday rentals with a kayak

4.99 out of 5 average rating, 95 reviews

A charming waterfront studio cottage is situated amidst greenery, featuring a white porch with steps leading to the entrance. The exterior is accented by large windows and a peaked roof, surrounded by landscaped paths and flowering plants under clear blue skies.

Guesthouse in Pocasset

Waterfront Cottage / Your Cape Escape

ValueLocationBarbecue

4.96 out of 5 average rating, 25 reviews

A charming exterior view of the studio apartment showcases a covered porch with white railings and hanging flower baskets. Lush greenery and garden plants frame the entrance, while a nearby building adds to the serene setting.

Apartment in Mashpee

Cape Cod Cottage Studio - Dogs are welcome

LocationValueSleep quality

A spacious dining area features a rustic wooden table surrounded by chairs, accommodating multiple guests. A stylish chandelier hangs overhead, illuminating the space. The adjoining kitchen is visible with modern appliances, and a window allows natural light to fill the room, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 65 reviews

Great Pond | Walk to Water, Hot Tub, Kayaks & Pets

LocationOutdoor spacesBarbecue

A serene waterfront view presents a vibrant sunset with colorful clouds reflecting on the calm water. Several outdoor chairs are positioned on a sandy area, offering a space to relax. The landscape is framed by trees, enhancing the natural surroundings.

4.96 out of 5 average rating, 93 reviews

Beautiful lakefront vacation property in Mashpee

LocationOutdoor spacesParking

A split-level ranch house is set on a well-maintained lawn adorned with vibrant flowers. A large rhododendron bush blooms next to the entrance, while small flags are placed in the grass, adding a festive touch. Lush green trees provide a natural backdrop.

5.0 out of 5 average rating, 13 reviews

The Happy Owl

LocationOutdoor spacesDecor

5.0 out of 5 average rating, 14 reviews

Home in Barnstable

Private Waterfront Escape | Kayaks + Firepit

LocationOutdoor spacesAccess

A charming two-story home is enveloped by a well-maintained yard and bordered by trees. The front porch features a white railing and a red door, complemented by neatly arranged landscaping. Bright sunlight illuminates the exterior, emphasizing the blue siding and inviting ambiance.

4.83 out of 5 average rating, 12 reviews

Pondside Haven

LocationOutdoor spacesCleanliness

A charming house is surrounded by lush greenery, featuring a pathway of stone leading to the entrance. Solar panels are mounted on the roof, and large windows allow natural light to fill the space. A small decorative birdbath is visible in the garden area.