Holiday rentals with a patio in Montauk

Serene w/ large pool, 1 block to waterfront dining

Make yourself at home at this chic serene Hamptons oasis! Located just 1 block to waterfront dining + 8 mins to Main St Enjoy your large private home nestled in nature w/ zen vibes. Hang poolside, spark up the firepit + BBQ, enjoy the outdoor shower, cook in your Chef's kitchen + stream on your 80' TV. Walk 1 block to waterfront dining + cafe to enjoy morning coffee on the sea + dinner + cocktails while watching the sun set over the harbor. You'll be 8 mins to Main St., beaches + so much more!

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!

Charming beach cottage perfect for families

Our house is steps from the beautiful beaches, restaurants/bars of Montauk Harbor and a 5-min drive to downtown/surrounding beaches. The house is 3 bd/2 full baths with a spacious living room, dining room, kitchen, fireplace, and bar nook. The backyard has a deck with a dining table, umbrella, grill, and lounge chairs - perfect for summer evenings! The house includes modern appliances, fast wi-fi, 2 desks, beach chairs/towels, bikes, and baby items (crib, nanit stand, changing table, bath tub)

Luxe Beach Cottage-Steps to Water-USGolf-Firepit

Kick back and relax in this calm, stylish beach cottage with NEW Kitchen and NEW bathroom (completed April 2026) 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 May-Sept. Beach chairs, umbrella and smiles!

Cozy & Relaxing 2-Bedroom

Comfortable 2 bedroom lower level of 2 unit home. MINIMUM NIGHT STAYS REQUIRED Your family will be close to everything when you stay at this centrally-located 2-bedroom home. Walk to town, Atlantic Ocean beaches, Fort Pond bay and access to off site pool. Unit is lower level of home. Fully independent of upstairs. Quiet & relaxing place to enjoy your time in beautiful Montauk. 2 car parking in driveway available. Dogs allowed for added fee with prior written approval by owner/host.

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

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Modern Farmhouse Oasis | Private Pool | Near Hamptons & North Fork Escape to a stylish sanctuary where modern design meets pastoral charm. Set on a private, one-acre land, this farmhouse is a masterclass in coastal living. Enjoy sun-drenched lounge areas, a sparkling pool, and the constant, cooling luxury of Atlantic breezes. Inside, the home offers a seamless blend of contemporary interiors, and high-speed Wi-Fi—perfect for a peaceful retreat or a "work-from-anywhere" getaway.

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.

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.

Montauk Poolside Suite, Steps to Beach

Escape to our stylish, second-floor coastal suite in Montauk, just steps from the sand! This bright, railroad-style retreat comfortably fits 4 guests. Enjoy a private terrace with pool views, fast WiFi, and easy access to the beach and town. Perfect for a sun-soaked vacation or a quiet getaway, with two pools available seasonally. Your ideal Montauk adventure starts here!

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.