Vacation rentals with a kayak in Dennis

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Popular amenities for Dennis kayak rentals

House rentals with a kayak

Superhost
A coastal cottage is shown, featuring a grey shingle exterior and a spacious front porch. An American flag hangs prominently on the facade. The sandy road leads to the entrance, with neighboring houses visible in the background.
Home in West Dennis
4.88 out of 5 average rating, 52 reviews

West Dennis Beach House - Steps to Beach

KelseyRating, 5 stars8 months ago
Renee’s house is absolutely perfect! It is directly on a beautiful private beach, and is close to all of the best bars and restaurants in the Dennis area. The house is equipped with anything you would need for a stay on the water: kayaks, beach chairs, beach toys, a water mat, outdoor showers, extra towels and a fire pit on a well-decorated finished patio. Unfortunately for us, we stayed during the first Nor’Easter of the season and were not able to use these, but rest assured we still had a GREAT stay. The house itself is immaculate: spotless and stylish, brand new appliances, spacious enough for a 6 adult family and all in all a great place to spend a cozy weekend inside. Given we could not sit at the beach, we leveraged Renee’s plentiful local recommendations and they were fantastic- we were not disappointed. If you are looking for a getaway on the water, you will love her place regardless of the weather. We would definitely stay again and would recommend to friends and family!
Guest favorite
A single-story home is set amidst a yard featuring a large, bare tree and low shrubbery. A paved driveway leads to a two-car garage with white doors. The exterior showcases a light blue siding and a brick facade, framed by patches of grass and a picket fence.
Home in South Yarmouth
4.9 out of 5 average rating, 21 reviews

Bass River Living: Community Dock, and swimming.

IlyaRating, 5 stars10 months ago
We loved Joe's place. The house is located in a clean, quiet and spacious community within reasonable drives to areas of Cape Cod that matter. Both Joe and Steven are amazing hosts. They treat you like friends, always willing to offer local advice. We had an issue that required Joe to come over to take a look and he was over in minutes. We definitely consider coming back next year.
Top guest favorite
Home in Chatham
5 out of 5 average rating, 18 reviews

Red Door Retreat in Chatham is 80% full for summer

AlexandraRating, 5 stars1 week ago
We loved this house. Perfect for a multi-generational family trip. Nice, private location with great yard and decks. House had everything we needed (and then some!). Kids loved the games in the basement and bunk room. Comfy beds, outfitted kitchen, multiple gathering spots. Ardys was a very thoughtful and responsive host. We will definitely be back!
Top guest favorite
Two kayaks, one red and one blue, are positioned on a grassy area next to the water. A serene view of the lake and a clear blue sky is visible in the background, accentuated by scattered clouds. A wooden lounge chair is placed nearby.
Home in Buzzards Bay
4.96 out of 5 average rating, 47 reviews

Oceanfront | Firepit | Gameroom | Pets | King Bed

BenRating, 5 stars3 days ago
Lovely spot near end of a cul de sac, great water views and light. Joel was proactive and responsive in communication.
Guest favorite
Home in Dennis Port
5 out of 5 average rating, 7 reviews

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

BarbaraRating, 5 stars7 months ago
Great spot to stay in Dennis. Quiet street , easy to get everywhere. The home was comfortable, very clean and fenced in yard was lovely. Amy was kind and communicative. Would love to stay here again next time we're back in the area.
Guest favorite
A bright living room features a white sofa with decorative cushions, arranged near a rustic coffee table. A cozy armchair and an ottoman are positioned nearby. Large windows allow natural light, while a fireplace adds warmth. Green plants enrich the space with a touch of nature.
Home in Barnstable
4.97 out of 5 average rating, 36 reviews

Cozy ranch with private neighborhood beach

AbenaRating, 5 stars1 week ago
We had a fantastic stay at this Cape Cod gem over Memorial Day weekend! The home was exactly what we needed for a relaxing family escape: clean, cozy, and incredibly well-equipped. From the moment we arrived, everything felt welcoming and easy. The hosts clearly put care into every detail, from the thoughtful amenities to the clear communication. Lauren was so responsive and helpful; and the gift basket with some goodies were well appreciated. It even had treats for our dog!! The location was perfect for exploring the Cape. We spent our days enjoying the beaches, despite the bad weather, charming local shops, and long walks together, then returned to a peaceful space where we could unwind as a family. Our toddler loved the backyard and the nearby private lakeside beach, and we loved having breakfast on the porch almost every morning. Everything was seamless and stress-free; a true rarity when traveling with a little one! We made lasting memories here and would return in a heartbeat.
Guest favorite
A newly built home is set among lush greenery, featuring a light wood façade and multiple large windows. A spacious driveway leads to a two-car garage. The entrance includes a welcoming set of stairs. A basketball hoop is visible on the right, enhancing outdoor recreation options.
Home in Barnstable
5 out of 5 average rating, 23 reviews

New Home 1 Bedroom and Bath Sleeps 4

JacquelineRating, 5 stars9 months ago
The house was cozy, clean, and a great place to stay for our time in Cape Cod. Steven is very responsive and we had a fun and easy time there.
Top guest favorite
A serene waterfront view is captured, featuring calm waters reflecting the sky with soft colors. Kayaks are positioned on a private dock framed by lush greenery and trees, creating an inviting atmosphere for outdoor activities.
Home in South Yarmouth
5 out of 5 average rating, 5 reviews

Spacious House on Long Pond - kayaks

LelaRating, 5 stars8 months ago
Perfection - no description or picture can capture this amazing property. Comfortable, tasteful, amazing activities and watercraft/beach supplies. Perfect for active boating, beach, cycling around or simply watching the swans and herons from the deck with a beverage in hand. We can't wait to come back. Main part of house perfect for 3-6 in the three comfortable bedrooms and the "rec room" bedroom perfect for 4 single bed sleeps (or just me - I had the bedroom deck to do yoga at sunrise and was sooooo happy). We wanted for nothing.

Cottage rentals with a kayak

Guest favorite
A spacious wooden deck features a single folding chair, providing a comfortable spot to relax. In the background, a scenic view of the tranquil lake is visible, surrounded by green trees under a clear blue sky.
Cottage in Falmouth
4.86 out of 5 average rating, 108 reviews

Spectacular Beach- front home, includes linen

LeticiaRating, 5 stars1 month ago
Our stay at Lisa's place was very pleasant. Her home is very nice with a lovely view of the lake and plenty of space for large families (we were only four people but can easily accommodate a few more). The neighborhood does not have a lot of car traffic which is great for walking and jogging around the lake. And it is also relatively close to Falmouth downtown and convenient stores. Lisa was very easy to communicate with and is very courteous and friendly. She really seems to care about her guests' comfortability. It was a pleasure dealing with her. Thank you, Lisa!
Superhost
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
4.81 out of 5 average rating, 31 reviews

Beach house- walk to ocean + 2 min to Craigville

JillianRating, 5 stars9 months ago
Our family had a wonderful time in Barnstable! Lynn and Ken were extremely responsive and did a great job at communicating when needed. The house was perfect for our family of three. Everything was clean and appeared exactly as the photos presented. We loved spending time on the screened in porch and the outdoor shower was a plus. Being less than 5 minutes from Craigville Beach was ideal along with the use of the beach pass. We would recommend this listing to anyone without hesitation and hope to book again for a future stay!
Guest favorite
Cottage in East Falmouth
4.94 out of 5 average rating, 170 reviews

“Cozy Cottage” on Great Bay

AngelaRating, 5 stars1 month ago
Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!
Superhost
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
4.92 out of 5 average rating, 129 reviews

Cape Escape-The Perfect Getaway

AlexandraRating, 5 stars2 weeks ago
We needed somewhere to stay for a wedding down the road. Kevin’s place was more than we were expecting! It was perfect! Clean and spacious. We will be keeping this top of our list for places to stay when on the Cape!
Top guest favorite
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
4.99 out of 5 average rating, 167 reviews

Little Boho Retreat by the Beach

RobertRating, 5 stars2 weeks ago
Felicia and Little Boho Retreat by the Beach deserve all the raving reviews. In all honesty I wish I could give more than five stars. The cottage is cozy, well-stocked, and every attention to detail is notable. Felicia thought of everything. The cottage is a destination in and of itself, to say nothing of the wonderful places we visited on The Cape, as well as Plymouth, Wareham, and Marion. I feel like there is so much more to do and experience on Dexter Beach and in this area. We definitely would like to return to this spot.
Superhost
The exterior of the condo duplex is showcased, featuring a shingle-style façade, a welcoming porch with a white door, and large windows. Lush greenery, including shrubs and a small tree, surrounds the entrance, enhancing the inviting appearance of the property.
Cottage in Brewster
4.82 out of 5 average rating, 11 reviews

Cottage near bay beach- 1 Bd/1Ba

GraceRating, 5 stars7 months ago
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!
Superhost
Cottage in Wareham
4.86 out of 5 average rating, 150 reviews

Onset beach, Cape code.Private Waterfront cottage

AkmRating, 5 stars1 month ago
We had such a peaceful and relaxing stay! The setting was incredibly serene, and we felt completely at ease the entire time. All of the amenities, especially the boats and kayaks, were very accessible, and we used them throughout our stay — it really made the experience special. We also loved spending cozy nights around the campfire, which added such a warm and memorable touch. There was so much for the kids to do, and they had a fantastic time as well! The host was so kind and welcoming, and communication was very easy from start to finish. Everything was thoughtfully prepared, and it made for a truly wonderful getaway. Highly recommend for anyone looking for a quiet, fun, and family-friendly escape!
Superhost
A serene view of the ocean at sunset is presented, with soft pink and purple hues reflecting on the calm water. A rocky jetty is visible extending into the water, leading toward the tranquil shoreline.
Cottage in Dennis Port
4.9 out of 5 average rating, 48 reviews

Ocean Front Cottage (7 nt. Min. stay July&Aug)

RichRating, 5 stars1 week ago
Lynda was very responsive. The cottage was as described and the beach was right there!

Quick stats about vacation rentals with a kayak in Dennis

  • Total rentals

    100 properties

  • Nightly prices starting at

    G$8,393 GYD before taxes and fees

  • Total number of reviews

    7.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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