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

The Hilltop Harborview
Very quiet and peaceful.

Romantic Couples Retreat with Private Sandy Beach
Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!

Sky of Blue, Sea of Green
This house had so many amenities and was exactly as described! We enjoyed having access to grills, a hot tub, game room, and all of the household/beach necessities! The house and game decor were super cute and the adults loved the competitive scrabble game on the wall. There was a small ant problem in the kitchen (which the owner was aware of) that was there despite attempts to keep the dishes and garbage can clean, but that was our only minor complaint. Overall, loved the place and would consider staying here again!

Oceanfront Retreat: Modern Beach House
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!!

Renovated Ranch Home wPool & Beach Acces
Beautiful home! Great location! Spent quality family time during Memorial Day weekend. So much to do on Northfork. Nicole was a pleasure to deal with.

Renovated Southampton Shores pool, tennis, beach
Lovely place for a long weekend with family! The house was pristine, up to date, charming, and all the linens were fresh and clean. It was very well stocked with kitchen essentials and books and toys for kids. Location also prime with a private beach a 10 min walk away. The only minor issue we had was an issue with the pool heating (it being the 1st pool weekend of the year) but this was sorted out promptly. Would happily stay there again!

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun
we had a quiet girls getaway to celebrate my sister getting married-upon arrival we checked out the entirety of the home…to which we were pleasantly surprised every corner we turned! exquisite home with comfortable, aesthetically pleasing furnishing and so much gorgeous natural light. the outdoor shower was a huge BONUS! heated pool had us outside moving our bodies more than we’d imagined and was such a fun way to spend time together. the living room is so cozy and a great space to have a game-night-in! i could go on and on about each detail but you should simply stay here and enjoy for yourself all this property has to offer!

Great Hammock Getaway | Beaches, Views & Hot Tub
This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.
Cottage rentals with a kayak

Lovely North Fork Beach Cottage (2 BR/2 bath)!
We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

Shelter Island Waterfront Getaway
Great stay, Maureen is very communicative and super helpful. Beautiful views

Pumpkins & Sunflowers! Cozy Cottage in the Fall!
Had a nice stay here with a group of people attending a wedding a short drive away.

Cheerful 3 Bedroom Cottage with Fire Place
We had a great stay at Jonathan's cottage. The location could not be beat - right on the beach. Jonathan was very easy to communicate with and quick to respond. There were a couple of minor hiccups that occurred but Jonathan was quick and responsive. Overall, a beautiful home in a great location.

Bellport Beach Estates Private Cottage with Pool
Had a great time despite the weather, there was so much todo. The place was cozy!

The Bay Breeze
Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

Guest House at the Marina
We absolutely loved our stay in Clinton! The apartment was beautiful and clean with an amazing view. We tried lots of local hot spots and had a great swim at nearby Hammonasset. Communication and instructions were excellent. We look forward to returning!

Cozy Cottage with Water Views Steps to the Sand
We had a great stay! The kitchen was nicely stocked and the house was clean. Plenty of outdoor space and beds made it comfortable even for a large group!
Quick stats about holiday rentals with a kayak in Southold
Total rentals
30 properties
Nightly prices starting at
₹15,582 before taxes and fees
Total number of reviews
570 reviews
Family-friendly rentals
30 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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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Dunewood
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park