Holiday rentals with a patio in Montauk

Secluded Luxury: New Gunite Pool, Walk to Bay

Welcome to the beautiful 5-bed, 3-bath Harbor House, located just a short walk from Gardiners Bay beaches. Enjoy open-concept living, fully equipped kitchen, comfy beds, gunite pool, private patio with gas grill & outdoor dining, hot tub, & fully fenced backyard. Walk/bike to harbor, rent kayaks, use our paddleboards, or explore nearby restaurants and shops. Whether you’re looking for a romantic getaway for 2 or a family vacation, our home is the perfect retreat for your next Hamptons adventure!

Serenity, large pool, 1 block to waterfront dining

Escape to you serene, chic Hamptons oasis! 1 block to waterfront dining + 8 minutes to Main St. Enjoy your privacy in this large property; swim in your pool, spark up the BBQ + firepit under the starry sky! Cook in your large Chef's kitchen and stream on your 80' TV. You can walk just 1 block to waterfront dining + cafe for delicious dinners on the sea. Enjoy the most magnificent sunsets in the area! You'll be 5-10 minutes to Main St. shopping, multiple beaches, coffee shops + so much more!

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Cheerful home with Heated pool and water views

Lounge by the heated pool enjoying the wonderful view of Fort Pond Bay or the ocean. The bedrooms consist of queen beds & Smart TV's, The Living room has 2 comfy couches, 1 of which also pulls out to a queen bed. Enjoy the wrap around deck & the backyard Washer/dryer, air conditioning, linens, bath, beach, and pool towels, as well as beach amenities including umbrellas, carts, & chairs It’s a 6 min walk to the ocean/town. There is also A playground and basketball courts right down the hill.

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Cozy Cottage

Tucked away on a quiet road, this cozy, plant filled cottage is the perfect home base for your Montauk adventure! If you are here for golf or tennis we are right around the corner from the Downs, for the beach lovers we are just one mile to Ditch Plains, a quick two to wander around town, or one and a half to jump on a boat in the harbor. This cottage was an original Old Montauk Highway cottage and was relocated in the 80s. It has been updated and very much loved over the years.

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hamptons! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

Charming Retreat Near Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Dockside 2BR on The Marina - Free Parking! Unit C

Roll out of bed, stroll 30 seconds to grab chowder, or hop on a charter right from the dock. This sunny Westlake spot nails the Montauk harbor experience — fresh interiors, good kitchen, and all your go-to eats within walking distance. Bonus: heated floors, fast Wi-Fi, and a TV for post-fishing relaxation.