Holiday rentals with a patio in Shelter Island Heights

Luxury Gem At The Heart of Sag Harbor Village

An impeccably renovated, luxury cottage at the heart of Sag Harbor village. Walkable within minutes to the downtown shops, restaurants, marinas and local beach! In one of the most coveted historic streets, enjoy this two-bedroom house, its large living & dining rooms, two fireplaces, designer kitchen (and latest appliances). Countless details and gorgeous wide planked floors, mixed with technology throughout the house. The private backyard has a brick patio, landscaped garden and outdoor shower.

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Bailey House

The Bailey House is a 1,900 square foot, fully renovated, 2 bed 2 bath home, with a modern rustic style. It has a working fireplace, baby grand piano, updated appliances, large smart tv and built in bluetooth speakers throughout. The backyard is fully fenced in with a pool, koi pond and barn. The barn has a wood burning stove. It is not insulated and has barn doors that do not fully seal it off from the elements. not included in square footage.

Private vacation home, close to beach

Welcome the our new Airbnb where serenity & style come together. Enjoy this charming, cozy home. Upon entering, you'll feel immediately relaxed & on vacation. This home is filled with natural sunlight light, large kitchen, stocked with with gourmet cookware & utensils. Outside you'll hear the babbling brook river, private large yard that offers outside patio deck for dining, entertaining or cuddling up by the fire pit.

Beach Cottage | Steps to Water | Firepit

Kick back and relax in this calm, stylish beach cottage 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, firepit/BBQ area, and my own tiny cottage across the lawn so I am readily accessible.

Hampton Studio

Keep it simple at this peaceful and centrally-located place.Fully equipped walking distance to town parks and restaurants.short drive to beaches. Totally separate from main house. Very private and quiet retreat.Queen size bed

Bay View Cottage- Short Walk to Private Beaches

Enjoy a stylish experience at this centrally-located mid-century modern cottage. 10 minutes to Sag Harbor Village, Southampton Village, Bridgehampton Villages. 5 minute walk to 3 beautiful bay private community beaches.

Coastal Cottage.

Family and Pet friendly 3 Bedroom home with fenced in yard and driveway parking on a dead end street. A few blocks to some great beaches and water access for fishing and Kayaking at the end of our road.