
Holiday rentals with a kayak in Oak Bluffs
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Top-rated rentals with kayak in Oak Bluffs
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
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House rentals with a kayak

Ready Oar Knot - Vacation is Here!
Christine and Sean’s place is an absolute gem. The house is filled with Cape charm and has everything you could possibly want or need for your stay. It’s walkable to multiple peaceful, beautiful beaches and is only a short drive from all the area has to offer. And most of all Christine & Sean are super thoughtful, responsive and always willing to answer any questions - it was my wife’s Cancerversary and they had a bouquet waiting for her inside. We will be back next year.

Snug Harbor - West Falmouth, Cape Cod.
Beautiful location, great house in good working order, friendly and responsive host.

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.

"Cape Escape" luxury home w/pool & beach access.
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !

Cape Cod Lake house home
The home was beautiful and thoughtfully stocked and decorated. It was spotless and the location was beautiful right across from a lake. The yard was gorgeous and the everyone loved the basketball, air hockey and foosball games in the garage. We will be back next summer!

Falmouth Summer Escape – Sleeps 6-Dog Friendly!
We have stayed at Brian’s place two years in a row, and it is by far the best airbnb we have ever stayed at. We love the amenities! Also, it is always incredibly clean and has super comfortable beds. Brian is incredibly responsive and accommodating, overall, an amazing host! We highly recommend staying here and plan to come back again!

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!

Waterfront Home in Centerville
This house is the perfect get away on the Cape! It has all the amenities needed to enjoy a house right on the water. The layout is perfect for both privacy and social interaction for a larger group. We used it to unite our family from around the country and it was perfect! Janelle was amazing and super helpful during our stay. Highly recommend!
Cottage rentals with a kayak

Seaside Cottage - Steps to Beach/Close to ferry
Exactly as described... And Sloane was incredibly proactive. The community had a water outage the morning we were due to check in and she contacted us immediately -- it was completely resolved before we checked in and she stayed on top of everything for us. Highly recommend visiting this cottage! Thank you, Sloane!

Waterfront Cottage - Waquoit Bay
Was exactly what we needed for a couple days with the family.

Cape Cod Retreat. Near Beaches and Swimming Hole
Ray...Thank you so much! Your rental home was beautiful and perfect for our family vacation a couple of weeks ago. Great location too for everything we wanted to do as well as close enough to visit with our local family in town. Having the ability to use your bikes were very helpful as we were able to just rent another two more which we used a lot to ride around Poppy. We would definitely stay here again. Thanks, Jessica SoCal

Cheerful 4 bedroom cottage in Woods Hole!
What a brilliant comfortable and relaxing time we had at Robert’s place. We had everything and more that we needed. Beautiful location, cosy and clean house, facilities top notch and comfortable beds. I could not say enough kind things about Robert! Responsive and pro-active, he made our stay even nicer with the loan of bikes. Thanks to him and his family we had a trip of a lifetime with my family. Unforgettable, hope to return again one day!

Marthas Vineyard Cottage - Path To Menemsha Beach
The place exceeded our expectations. The location is incredibly peaceful, with stunning west-facing views—perfect for watching sunsets. We stayed with our two dogs, and the walk to the beach was absolutely gorgeous. Just a short stroll through a meadow and forest leads you to a beautiful beach and one of the best fish markets on the East Coast. The variety of seating options is fantastic—you can relax on the grass in front of the house, lounge on the porch, stay protected from insects on the covered patio, or get cozy inside. We’ll definitely be coming back. We loved our stay and made some truly beautiful memories.

* Rustic Cape Cod Captain's Quarters Cottage
It is a lovely holyday flat A bit old but totally fine. More space then expected and everything needed was available.

“Valhalla” on West Island
We had a great time, thanks!

Beach front cottage, water views, WIFI
We liked this place so much that we visited the second time. Great location - right on the beach. The pier is right in front of the house and looks scenic right from the sun room. Wake up early enough and you can see the sun rise on the ocean from the sun room. A private beach is right around the corner. Being private, it's never crowded. It is sandy and does not have stones and pebbles like the rest of cape cod. Being inside, the water does not get too cold. Gets some waves during high tide and can be calm and serene during the low tides. During high tide, you can also dive from the pier. The house also comes with couple kayaks with life jackets, chairs, some beach toys - everything you would need on a beach. The yellow kayak is good. The blue one seems for kids. I toppled once trying the blue one. They also have some old bikes - not in the best condition, but they work. The house is very old. A lot of the doors don't close properly and can't really lock them.
Quick stats about holiday rentals with a kayak in Oak Bluffs
Total rentals
30 properties
Nightly prices starting at
₹12,923 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Roger Williams Park Zoo
- Owen Park Beach
- Point Judith Country Club
- Coast Guard Beach
- Oakland Beach
- Onset Beach
- Inman Road Beach
- South Shore Beach
- Nickerson State Park
- Fort Adams State Park
- Second Beach
- Oyster Harbors Beach
- Pinehills Golf Club
- Goddard Memorial State Park
- Scusset Beach