Waterfront vacation rentals in Southampton

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, sweeping staircase, 5 bedrooms plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed Jan-March)

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a swim and outdoor shower after a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons.

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

Beautiful Waterfront Cottage

Historic Waterfront with Private Island (this property has a bridge to a private island). Large south facing deck, brand new kitchen and beautiful antique claw-foot bathtub and rainfall shower. The home is 10 minutes from the beach, 10 min from Bellport, 25 minutes from Southampton and 1 mile from the train station to New York City. Enjoy a quiet escape from the city in this well-appointed home.

Waterfront Beach Cottage

Four bedroom beach cottage with direct waterfront. Built in 1910 and maintains its original charm. Sit on the beach or front porch enjoying the views of Long Island Sound. Beach is great for swimming and playing. Perfect for a family vacation or long weekend getaway!

Ritz-East Hampton Cottage- 5 stars

Separate 2 Bed/2 Bath guest cottage on a private family compound. Enjoy beautiful sunset views and a cool breeze located on a 5 acre waterfront property with a natural Marina, overlooks 100+ acre nature preserve. Please read the 300+ perfect reviews