Vacation rentals with a kayak in Southold

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck, complete with a Weber grill. Vaulted ceilings and large windows flood the space with natural light. We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are open for the season and will close by mid September 2025.

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Cottage by the beach

Relax with the whole family at this peaceful place to stay with water views. Enjoy the beautiful outdoor living space including a large patio with plenty of seating for eating and entertaining. Outdoor shower, Weber grill, fire pit, kid games, kayaks, paddle board to name a few. Short walk to the beach. 2 bedroom 1.5 bath, comfortable living room and eat in kitchen, central air. Private block, close to farms, wineries and town.

Peaceful Guesthouse

This oasis includes 2 bedrooms including a pack and play. sleeps 4 adults comfortably. 1 bath and a half. Kitchen, dinning room and living area with fireplace. An additional dining/sitting area on outside patio with an additional fireplace. The house is 1/2 mile walking distance from beach, 1 mile from eateries, 3 miles from local winery and brewery. Choice of golf courses within 5 mile radius. Certification Number: 1028

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...