Holiday rentals with a patio in Southold

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

Southold Home with Saltwater Pool (until 10/13)

Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater heated pool, cozy fire pit, BBQ area, and ample outdoor seating. Ideal for family getaways or group retreats, the house is just minutes from renowned wineries, beaches, and charming local farm stands. With bright and spacious living areas, this home offers a perfect blend of comfort. Whether lounging by the pool or exploring wine country, experience the ultimate North Fork retreat!

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Beachfront Greenport Villa

Welcome to Villa Sonore. A gorgeous beachfront villa in Greenport located right on the LI Sound. Walk to restaurants and bars at the Soundview. Bike to North Fork wineries, breweries, farms and town. Or just relax on the enclosed porch or back deck and take in the magnificent views of the beach. Listen to the waves crash and enjoy views of the water that can only be rivaled by being out at sea! Paddle boards, bicycles, beach chairs and an umbrella are provided for our guests. Enjoy!

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Gorgeous home with saltwater pool. Steps to beach!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Salt & Sea House - Near wineries, farms, & beaches

Escape to Paradise at the Salt & Sea House! ☀️🌊 Indulge in a luxurious North Fork retreat, just moments from pristine beaches, world-class wineries, and charming farm stands. Unwind in the expansive yard, soak up the sun, and savor breathtaking sunsets. Inside, you'll find a chef's kitchen, cozy living room, and a dedicated workspace for ultimate productivity. Family-friendly with a Pack 'n Play & toys. Book your dream getaway today! ✨

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.