
Vacation rentals with a kayak in Dennis
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Top-rated kayak rentals in Dennis
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House rentals with a kayak

West Dennis Beach House - Steps to Beach
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!

Bass River Living: Community Dock, and swimming.
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.

Red Door Retreat in Chatham is 80% full for summer
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!

Oceanfront | Firepit | Gameroom | Pets | King Bed
Lovely spot near end of a cul de sac, great water views and light. Joel was proactive and responsive in communication.

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

Cozy ranch with private neighborhood beach
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.

New Home 1 Bedroom and Bath Sleeps 4
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.

Spacious House on Long Pond - kayaks
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

Spectacular Beach- front home, includes linen
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!

Beach house- walk to ocean + 2 min to Craigville
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!

“Cozy Cottage” on Great Bay
Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!

Cape Escape-The Perfect Getaway
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!

Little Boho Retreat by the Beach
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.

Cottage near bay beach- 1 Bd/1Ba
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!

Onset beach, Cape code.Private Waterfront cottage
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!

Ocean Front Cottage (7 nt. Min. stay July&Aug)
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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- New Silver Beach
- Onset Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Inman Road Beach
- Kalmus Park Beach
- Ridgevale Beach
- Cahoon Hollow Beach
- Minot Beach
- Peggotty Beach
- Lighthouse Beach
- Forest Beach