Holiday rentals with a patio in Montauk

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

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!

Montauk Surf Cabin with Deck on a Nature Preserve

Relax and enjoy the best Montauk has to offer at this peaceful, comfortable, and stylish cabin. With 4 BR and 2 BA (one en suite in the primary), everyone has space and comfort in this gem of a home. Out back, overlooking the nature preserve, you'll find a large deck with lounge seating, a huge dining table and an ice plunge and sauna. Only about a mile from Ditch, Town and the Dock, at the end of a private gravel road, this unique space is the perfect location for you and your friends or fam.

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.

Designer home in Sag Harbor : 5BR walk to beach

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Renovated Oceanfront Montauk Studio Retreat

Experience the ultimate Montauk getaway in this stylish, renovated oceanfront studio. Perched on the 2nd floor, your private balcony offers front row seats to the Atlantic-keep your eyes peeled for dolphins and whales which are frequently spotted right from the unit! Whether you're grabbing a lobster roll from the award winning food truck, dipping into the indoor pool or ending your night with a private bonfire on the beach, this is the perfect place for your east end escape.

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.

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468

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 House close to 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.

Center of Town + Ideal for Beach, Golf & Tennis

Our home is centrally located in Montauk. 5 minutes +/- from everywhere you want to be. Montauk Downs State Park is directly across the street, providing public access to golf, tennis, pickleball, swimming and a patio bar/grill that overlooks the golf course. Quiet neighborhood + private backyard setting. Convenience and relaxation at its finest!