Family-friendly vacation rentals in Orient

Quiet, Upscale Retreat by the Beach with NEW Pool

We're on a quiet, tree-lined street, a lovely bike ride or walk from a pebble beach, with crystal clear water and stunning sunsets. Our house is the ideal base to explore the North Fork, where bucolic farmland abuts magnificent beaches. We're 5 minutes by car or 15 by bike to the charming seaside villages of Greenport and Orient. Our house is fully stocked, newly renovated and the spacious backyard borders 10 acres of lovely forest preserve. No large groups of unrelated adults. Brand new pool!

Sag Harbor / Noyack Pad - private STUDIO apartment

500sq ft studio apartment, with private entrance, private bathroom, outdoor deck area with table/chairs, private kitchenette (but no stove). Close to Noyack Bay/Long Beach. 5 min drive to Sag Harbor village. 15 min to East Hampton village. 15 min to Ocean beaches. Responsive host: you will be greeted and handed keys when you arrive. No waiting around. Host will respond to all calls or messages rapidly if any issues arise. Lockbox entry with spare key also for 24 hour access

Aqua Vista

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

1830 Historic garden wing - walk to it all

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Cozy Loft Getaway

Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

Designer East Hampton Farmhouse - Cozy Fall Vibes

Tucked away on a private lot, just minutes from East Hampton Village, Amagansett Village, and Ocean Beaches this 3-bedroom, 2.5-bath cottage features a heated saltwater pool & Mahogany outdoor shower, outdoor lounge area, and charming children’s playhouse - creating the perfect setting for relaxing days spent at home.