Vacation rentals with a kayak in Shelter Island

4.84 out of 5 average rating, 107 reviews

A charming cottage exterior is presented, featuring a light yellow facade with contrasting black shutters. A vibrant red door provides a welcoming entrance. Lush green shrubs and seasonal flowers frame the walkway, enhancing the overall appeal of the front yard.

Home in Hampton Bays

Heart of the Hamptons

Peaceful 3 bedroom cottage in a quaint section of the Hamptons. Located on the south shore, closest to the ocean beaches you can get. Bay water at end of lane, ocean beach just over the Ponquogue bridge. Large backyard for games & BBQ grilling. Enclosed patio for morning coffee & evening dinners. The house is best suited for families & friends needing space & looking for simple, low key relaxation. Please click "Contact Host" if you have specific booking requests & I will look to accommodate.

Guest favorite

A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

4.88 out of 5 average rating, 26 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

4.87 out of 5 average rating, 90 reviews

A light-colored boat is anchored in calm water, surrounded by lush greenery. Reflections of the boat can be seen on the still surface, while distant homes are visible along the shoreline under a clear blue sky.

Cottage in Southampton

Waterfront Beach Home & Garden —AC, BBQ, Kayaks!

Directly on the water! And minutes from sandy beach 🏖️ and exquisite sunsets — ideal location midway Sag Harbor and Southampton. AC & well equipped country kitchen in renovated 1920’s two bedroom cottage. Master bedroom with glass sliders look onto sun-kissed sea. Adirondack chairs surround fire pit overlooking the swans that drift by. This is a tranquil hideaway in the Hamptons. Launch a guest kayak - with life vest pfd — from garden or simply drink in the great views.

5 out of 5 average rating, 102 reviews

The exterior of the home showcases a two-level structure with large windows illuminating the living spaces. An expansive deck with outdoor seating invites relaxation. A kayak rests on the lawn near the well-maintained landscaping, promoting fun activities by the water.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

An aerial view provides insight into the waterfront cottage's layout, showcasing the grassy yard surrounding the home. A patio area with seating is visible, alongside a garden shed and trees offering shade. The peaceful lake borders the property, enhancing the serene environment.

4.89 out of 5 average rating, 37 reviews

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

Guesthouse in Southampton

A modern two-story building is viewed from the well-maintained lawn. The heated saltwater pool features clear water surrounded by lounge chairs under colorful umbrellas. Lush green trees provide a natural backdrop, creating a peaceful outdoor space for relaxation.

4.98 out of 5 average rating, 65 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

5 out of 5 average rating, 24 reviews

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

The image presents a coastal view featuring a well-maintained property adjacent to the shoreline. The sky displays a gradient of colors at sunset, and gentle waves can be seen lapping against the rocky beach. Surrounding greenery complements the tranquil setting.

4.86 out of 5 average rating, 22 reviews

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

Guest favorite

A serene beach scene is captured at sunset, featuring soft, warm hues in the sky blending with the calm water. The sandy shore curves gently along the edge, with distant islands visible on the horizon, creating a peaceful coastal atmosphere.

Home in Sag Harbor

4.95 out of 5 average rating, 21 reviews

Beach Cottage | Steps to Water| Fireplace|Firepit

Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in August/September/October stays). Firepit area is shared with Bouy Cottage.

The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.

5 out of 5 average rating, 14 reviews

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

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱