
Vacation rentals with a kayak in Oak Bluffs
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Top-rated kayak rentals in Oak Bluffs
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House rentals with a kayak

Beautiful Mashpee Home with Pool
The house was beautiful, better than expected! It was very spacious with lovely high ceilings in all the rooms. the bedrooms were all large and delightfully decorated, as were the two sitting rooms. In fact the layout worked really well for our family group: master bedroom with en suite for us grandparents, first floor bedrooms for one couple and their two kids with shared bathroom and extra sitting area with TV, and the garden room -with an enormous bed!- and ensuite bathroom for the other couple. The pool was a very good size with comfortable loungers and the large table on the terrace was perfect for mealtimes. The kitchen was fully equipped and there were an enormous range of dishes and utensils! The various beaches we visited were all within easy reach and Mashpee Commons was only a short drive away with a range of restaurants and shops. Nicole was very responsive and answered our questions quickly. We had a wonderful time and the house exceeded our expectations!

Dog-Friendly Hatchville Escape for 6–April Awaits!
This was our second stay at the hatchville home and it was just as great as our first time! The home was clean, bathrooms were spotless and the living spaces were warm and inviting for the holidays. Thank you, Brian for your hospitality! Highly recommend this home.

Mashpee Manor Pool House
House was very clean and comfortable. Kathleen was very responsive to all my inquiries both prior to and during our stay. House was easy drive to shopping and dinning as well as the local ponds and beaches. Although we did not cook if u plan to prepare meals be aware kitchen has limited pots and pans for cooking. Also would have like to have a tea pot to boil water. Otherwise had everything we needed for a wonderful stay

Spacious 4-Bedroom home with outdoor dining
Sue is an outstanding host and this home is a gem in the Martha Vineyard area. I highly recommend staying here if you ever get the chance! The surroundings are beautiful and the area is quite peaceful. It is also quite convenient and right next to a bus stop (google maps was wrong about the bus route from Martha’s Vineyard).

Greenehill~ Up-island 1800's Vineyard farmhouse.
We stayed over the long weekend at this beautiful property. It’s located centrally close to all the major attractions and beaches. The property had beautiful features and felt very comfortable. The home itself had a lot of charm and had a positive energy. Hosts were very kind and nice to communicate with. They left us wonderful treats and fresh eggs from their beautiful garden. Overall it was a great stay at their property. Highly recommended and we will be staying there again. I will highly recommend getting a car to travel in the island so you can go to Edgartown or other places.

Beautiful Edgartown Colonial with heated pool.
This house is literally perfect! It was clean, spacious and well stocked. The house is in a quite neighborhood which made it even more relaxing. The pool exceeded all expectations and I hope to have the opportunity to go back next year!

Kayak to the OCEAN from your own backyard!
Very comfortable for 6 adults. Full kitchen with every utensil, pot, pan, and appliance imaginable, all clean and in like-new condition. Beautiful deck, great for Happy Hour and family dinners. Beds were comfy. Bathrooms had spa-like showers. Enjoyed the bikes and kayaks. Everything high quality and in excellent condition. Outside shower was nice for rinsing off the sand. Hugh TV and ability to login to our YouTubeTV account was a bonus. Lots to do: town beaches close by, Cape Cod Winery, highly recommend Betsy's Diner for breakfast (lots of gluten free options), Shipwrecked for Happy Hour, strolling Main Street Falmouth, Shining Sea Bikeway, and great local parks and conservation areas with walking trails. Our family and dogs enjoyed a great vacation. Highly recommend Jennifer's home even if you're not traveling with pets.

Newly Renovated Home! Hottub! Walk 2 beach! Slps 9
My girlfriends and I have been friends for 15 years and this is the first time we've been able to plan a girls weekend away. Kimberly was responsive, helpful, and great throughout the entire process. The home was exactly what we anticipated and had everything we needed for a fantastic weekend away. The only issue we had was a noise complaint Friday night, where a neighbor went direct to Airbnb. The complaint filed was for a time we were already inside well ahead of quiet hours. We brought this to Kimberly's attention and she was highly responsive and attentive to resolution. We enjoyed our time at this home and the only caution is being mindful of the neighborhood as it felt more like Airbnb guests were less than welcome.
Cottage rentals with a kayak

Spectacular Beach- front home, includes linen
Excellent stay. Plenty of room for the 5 of us. We rested well and were able to relax. We appreciated having laundry on site since we were on a 10-day trip. The beds were comfortable and we slept well. But that is a minor detail when you can watch the sunset over the peaceful water. Lisa communicated well and responded quickly. The house is easy to get to and stores are easy to travel to. Excellent location.

Compass Rose Cottage ★ Steps to Flax Pond & Trails
As soon as I walked into Carol’s place, I felt right at home. In fact, I was sad I couldn’t stay longer. Dennis is a great centrally located area on the Cape (next to many great restaurants and a supermarket). The cottage itself is in a quiet neighborhood right in front of Flax Pond (great for kayaking). It was well stocked with amenities and things to do I could just spend all day there. Carol was friendly and responsive. I would book at the Compass Rose Cottage again!

★Waterview ★Pet Friendly ★Kayaks ★Trails ★
We had a wonderful stay at Victoria’s place. The cottage was very clean and had everything we could need. We love that it is pet friendly as our dog travels with us everywhere. We love the extra added touches of treats for us and our dog. The lake and surrounding area is absolutely beautiful and the neighborhood was very peaceful. This is our second stay at Victoria’s place and we will definitely be staying again!

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS
We had a great week staying at this cottage! It was just what we needed for some time away: cozy, friendly and peaceful environment close to the bike trail and restaurants. We highly recommend!

Kayaks and Glimpses of Westport Bay
Linlin was a wonderful host and we loved this adorable cottage. It was incredibly clean, while still being warm and welcoming for us (and our pup). It's a little farther from the water than we had anticipated, but it's a relatively short and private walk to a dock with kayaks and beautiful views. Highly recommend!

Serenity Views | Waterfront | 7min2Beach | Kayaks
A Perfect Stay – Cozy, Clean, and Wonderfully Hosted We had an absolutely delightful stay. The space was clean and equipped with all the amenities needed for a comfortable visit. The location was ideal—peaceful and serene yet conveniently close to local attractions and dining options. What truly set this experience apart was the host’s exceptional hospitality; they were incredibly responsive, accommodating, and made us feel right at home. Look forward to returning!

Cape Escape-The Perfect Getaway
Great Dennisport cottage! Walk to Chapins, walk to Glendon Road Beach. Great amenities and well supplied. Perfect place for a weekend getaway.

Local Beach+ Fireplace + Hot Tub Under the *Stars*
We had such a great time visiting Cape Cod. Christina was an awesome host, and the home was lovely. My kids loved the hot tub, and the costal decor. I appreciated the well stocked kitchen and personal touches. Great mid cape location!
Cabin rentals with a kayak

The Flamingo House @ OBC Beach Resort and Habitat
The cozy venue is beautifully located, offering all the comforts of a small Cape Cod cottage on the salt marsh. The hosts were incredibly welcoming, ensuring that everything was available for a comfortable stay and making themselves accessible at any time. I highly recommend this place to anyone looking for a super unique, peaceful retreat that has convenient access to endless activities. The property is situated in a unique, serene location with easy walking access to local parks and a variety of quality restaurants. The water is perfect for paddling to explore the large area of connected coves. It’s a short distance to the Cape Cod Canal Railroad Bridge and the canal trail. There's little need to leave the property but there is much close by to explore. I'm looking forward to returning to experience everything again, and maybe, experience and discover even more next time.

The Crab House @ The OBC Beach Resort and Habitat
Thank you to our wonderful hosts at the Onset Compound for an incredible stay! The home is located in a picture perfect waterfront setting with all of the amenities a beach house offers. The hosts recommended some great restaurants and things to do that kept us busy all weekend. The home is sparkling clean and we felt right at home!

The Birdhouse - tiki hut in nature
The Birdhouse was a delight. I had a wonderful night’s sleep. Martha is a gracious and helpful host.
Quick stats about vacation rentals with a kayak in Oak Bluffs
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ551 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 National Seashore
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Roger Williams Park Zoo
- Nickerson State Park
- Oakland Beach
- Grey's Beach
- Chapin Memorial Beach
- Coast Guard Beach
- Scusset Beach
- Corn Hill Beach
- Pinehills Golf Club
- South Shore Beach
- Earle Road Beach
- Cahoon Hollow Beach
- Baker's Beach Club
- Fort Adams State Park
- Salty Brine State Beach
- Agawam Hunt
- Rocky Point Beach