Holiday rentals with a kayak in Long Island Sound

Find and book unique kayak rentals on Airbnb

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Popular amenities for Long Island Sound kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Guest favourite
Home in Greenwood Lake
4.97 out of 5 average rating, 186 reviews

The Best Lake House! *Ask About Boat Use Promo*

KevinRating, 5 stars1 month ago
This beautiful lake house is a lovely retreat from the chaos of the city. We spent the day lounging by the dock, and relaxing in the sun. It was awesome to have a full private bar with your own pool table right in the house!
Superhost
Home in East Haven
4.96 out of 5 average rating, 100 reviews

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago
This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!
Top Guest favourite
Home in Milford
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Top Guest favourite
Home in East Marion
5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

SamanthaRating, 5 stars1 month ago
Can not recommend more! Beautiful house and perfect location! Would love to come back. Kids loved the beach and finding shells and little sea creatures in low tide!
Guest favourite
Home in North Stonington
4.96 out of 5 average rating, 122 reviews

The Perch

DeniceRating, 5 stars7 months ago
I have stayed at lots of places in the last few years . . . and this place ranks right at the top. It is beyond beautiful. The water views from the living room and both bedrooms made it hard to leave and come home. It's actually even more amazing than the pictures. Don't think twice! Book this place now!
Guest favourite
Home in East Haven
4.95 out of 5 average rating, 40 reviews

Direct Beachfront Modern Cottage on Private Beach

MacKenzieRating, 5 stars3 weeks ago
We had a great stay at the Airbnb. One thing I haven’t seen mentioned in the reviews or descriptions is that this beach had tons of sea glass! In our short stay we found over 100 pieces and my 4 year old was absolutely delighted scouring the beach for it. There are also tide pools less than a five minute walk from the house. These two things made the stay quite magical for my kids. Otherwise the location is great and the house was very clean. I appreciated the bed on the first level having a trundle as well as a door at the top of the stairs for safety. The house is minimally decorated which is honestly a plus when you don’t have to worry about your kid breaking nicknacks on coffee tables. A few nice throw blankets and nicer glassware would have added to the stay though. Overall we were very happy with this property.
Guest favourite
Home in Milford
4.94 out of 5 average rating, 33 reviews

Charming 3 bedroom Beach Front Cottage

AlanRating, 5 stars3 weeks ago
Great weekend! The house is located, right on the water. The layout is perfect for our group, 4 kids 6 and under, parents and grandparents. We would stay here again.

Cottages with a kayak

Guest favourite
Cottage in Putnam Valley
4.96 out of 5 average rating, 166 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

MadelineRating, 5 stars2 days ago
Benjamin's place is all you expect and more. It is clean, roomy, comfortable, and quiet. My family is all about comfortable temperatures and the AC makes each room feel great. If you are sitting on the deck, off the kitchen, there is a breeze with pretty sunrises and sunsets. Ben was a thoughtful host! I reached out with one simple question and before we knew it we had items delivered to the door - for our family and our dog! It was a delightful and welcoming touch. The cottage is so comfortable with fabulous bedding, a fantastic Jacuzzi tub, a fully stocked kitchen, and a full coffee and tea bar! Such a generous amenity. I highly recommend Benjamin's cottage.
Superhost
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars3 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Top Guest favourite
Cottage in Shelter Island
4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

CindyRating, 5 stars6 months ago
Great stay, Maureen is very communicative and super helpful. Beautiful views
Guest favourite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 354 reviews

Be in Nature at this Gorgeous Riverfront Cabin

MJRating, 5 stars6 days ago
A lovely home with beautiful views of the surrounding woods from each room. Very clean, modern, and comfortable with a well stocked kitchen. Mark provided detailed and useful info on the place and the surrounding area. A great spot if you’re looking for some peace and quiet close to all the local attractions of the Hudson Valley.
Top Guest favourite
Cottage in Shelter Island
4.96 out of 5 average rating, 107 reviews

3 Bedroom Cottage Gem

MontagueRating, 5 stars1 week ago
Loved our stay! This is a gem of a house—it’s gorgeously decorated and equipped with everything you need to feel immediately at home. Shelter Island is one of my favorite places and this home made it feel all the more special. Thank you, Christopher!
Top Guest favourite
Cottage in Guilford
4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

KitRating, 5 stars3 days ago
A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.
Top Guest favourite
Cottage in Highland Lakes
4.97 out of 5 average rating, 327 reviews

The Mountaintop Lakehouse that Time Forgot.

MaryBethRating, 5 stars3 weeks ago
Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go back again.
Guest favourite
Cottage in Montville
4.95 out of 5 average rating, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

NicoleRating, 5 stars3 weeks ago
Fantastic! The cottage is cozy and clean, had everything we needed and the views are gorgeous! We loved our stay and highly recommend this beautiful cottage!

Cabin rentals with a kayak

Guest favourite
Cabin in Ferndale
4.92 out of 5 average rating, 223 reviews

Charming Catskills Lakefront Home—2 hrs from NYC!

MatthewRating, 5 stars1 week ago
Jill’s place was beautiful , cozy and unique. She was very accommodating with any questions we had, and the area had lots to offer. We drove through the mountains, checked out the historic Woodstock grounds, and went to many of the really cool breweries that were suggested. We also really enjoyed playing many of the records that she had while enjoying sunsets from the lake view of the house. Definitely would recommend and would love to come back for a visit
Guest favourite
Cabin in Greenwood Lake
4.99 out of 5 average rating, 89 reviews

Modern Nordic Designed Cabin

FeRating, 5 stars1 week ago
The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!
Guest favourite
Cabin in Huguenot
4.94 out of 5 average rating, 269 reviews

Tranquil Lakefront Cabin!

CaleRating, 5 stars3 weeks ago
Very nice house, good fishing and wildlife nearby. A little closer to the neighbors than expected, but overall a great place and would love to come back
Guest favourite
Cabin in Webster
4.91 out of 5 average rating, 168 reviews

The Camp

TorRating, 5 stars3 weeks ago
We truly enjoyed our stay at Karin’s place. She is a gracious host. There were great cottage offers beautiful lake experiences, including beautiful sunsets. She has a great waterfront and an expansive yard. It’s located on the Massachusetts, Connecticut and Rhode Island border with easy access to 3 states.
Superhost
Cabin in Wantage
4.85 out of 5 average rating, 136 reviews

ECHO cabin - lakefront peaceful modern house

VictoriaRating, 5 stars7 months ago
Very cozy, private, clean and feellikehome spot. Beautiful house on the lake with everything you need. Definitely would stay there again and recommend to everyone who is looking forward for a little getaway from busy life. Great host, responds quickly if any questions, clear instructions and info made my stay super comfortable and memorable. Great experience.
Superhost
Cabin in Kerhonkson
4.93 out of 5 average rating, 164 reviews

Cozy Cabin with Pond on Six Acres

JayvonRating, 5 stars4 months ago
We had an amazing valentines weekend and my dog couldn’t have had more fun ! This private cabin in the neck of the woods can truly be described as a real getaway ! It has a beautiful landscape and is strapped with everything we needed and more. After a full day of hikes in the local area, we found ourselves snowed in and enjoyed some card games. We had an outdoor fire in the stone pit and made some smores. Colleen and Julian were also super accommodating for us due to the weather conditions as well. They are beyond helpful ! Thank you guys ! Will definitely be back !
Guest favourite
Cabin in Coventry
4.88 out of 5 average rating, 136 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

MariaRating, 5 stars1 week ago
Joe's Cabin was exactly as described in the listing. Beautiful, peaceful neighborhood, and right next to the lake. Our family came into town for an event and the cabin was the perfect place to relax and unwind. Every part of the home was clean, beds were very comfortable, and every amenity was available if needed. Host was very responsive and communicated well. We will definitely be back.
Top Guest favourite
Cabin in Voluntown
4.95 out of 5 average rating, 743 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

ChristineRating, 5 stars6 days ago
Great camp and peaceful area. Angela is a great host and very accommodating. I have stayed twice and would definitely come back again.

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