
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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House rentals with a kayak

Tranquility at the Water’s Edge
This place was divine. We came for a week with our two kids (4&6) and had the easiest most laid back time. We kayaked, walked to the beach, the kids played constantly around the house as it’s right on the water but the yard is fenced off. It was so good you guys 10/10 would book again. And Jeff was the best host. So quick to respond, provide options etc. He rocks.

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!

Private Beach access along the Wine Trail
I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Waterfront home with amazing views
Frank was very accommodating! He even offered an extra night or a late check out which was extremely generous. We appreciated how little we were asked to do before check out, it always feels like we have to clean the house top to bottom before checking out of anywhere we stay on Airbnb. We will definitely book again!

Private and tranquil Holiday retreat.
Our stay at 129 Bull Path exceeded expectations serving us well for a peaceful and relaxing getaway. The kitchen is well stacked for your cooking needs and we found ourselves spending more time in it and the dining area cooking, eating and having great conversations. The basement is also well equipped and the entire house is as functional as it’s beautiful. Peter our host was very responsive and nice, he provided clear instructions and gave great recommendations as well.

Cozy home. Comfy living
Steve went the extra mile to help me during check out. My ride was running late and my one year old daughter was sleeping. He was lovely and understanding.

Beautiful Hilltop Property on Shinnecock Hills
Jeans place was gorgeous and the perfect size for our group of 8! Close to the town square and restaurants. Incredible backyard and views, great for family vacations and group getaways! Thank you jean!
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.

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

Stunning waterfront modern farmhouse with dock.
This beautiful piece of heaven was better than we could have imagined. As beautiful as the pic are, they don't do justice to the serenity of this property. Our group already decided to come back again. Michelle was lovely and thoughtful. The house was stocked with all the essentials and more. The coziness was unbeatable. We had the best weekend with the best friends.

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.

Secluded Soundfront 1910 Rustic Getaway
The house’s location was amazing and exactly as described. It was great having the beach in the backyard and being able to swim whenever I felt like it. There were plenty of areas to sleep, eat and sit either as a group or individually. The house was well stocked with anything you could need. I had an issue and Joseph responded and took care of it super quickly. There’s a lot to do in the area, but I didn’t get to a lot of it because I was enjoying the property so much.

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!

Prime village location, walk to Main St, prvt yard
This is such a great, cozy place in an unbelievable location. I spent the night with my daughters for Father’s Day. We BBQ’d a feast in Erica’s backyard. Coffee in the morning literally just around the corner in the town of Westhampton. We didn’t have beach weather but the cottage was clean, relaxing, and we all enjoyed. I would definitely stay here again.
Quick stats about holiday rentals with a kayak in Southold
Total rentals
30 properties
Nightly prices starting at
$232 SGD 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
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park