Vacation rentals with a patio in Shelter Island Heights

Serene w/ large pool, 1 block to waterfront dining

Bask in your totally private + serene home w/ large pool, located 1 block to waterfront dining. Swim all day, spark up the firepit + BBQ, enjoy dining under the stars! Relax in the abundance of nature and greenery surrounding the home. Take a stroll 1 block to the best waterfront dining + cafe where you can enjoy your morning coffee overlooking the sea + have cocktails and dinner watching the sunset. Come home + stream on your 80' TV. You'll be 8 mins to Main St., shopping, beaches + more!

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

Enjoy this newly renovated 2 bedroom 2 bath loft apartment centrally located in the village of Greenport. Conveinient 5 minute walk to Front street, Main street shops, restaurants, bars and across from park/playground. Private rear deck for outdoor dining and a covered front porch for a glass of wine or morning coffee. Parking for 2 midsize cars in driveway. Power outlet available for EVs. Private yard with BBQ, firepit, adirondack chairs grassy area and lounges for sunning, reading or napping.

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!

Luxe NEW Beach Cottage-Steps to Water-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!

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

This cozy cottage is perfect place to relax and unwind. Located in the center of the island about a mile from the beach and nature preserve. Sleeps up to 9 people - with queen size aero bed provided. Linens, dishes, utensils etc. included. Fridge has icemaker and filtered water feature. Outdoor covered dining area with table and 8 chairs. 2 person swing, BBQ & outdoor shower. 2/3 acre property. Relax with the whole family at this peaceful place to stay.

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Hamptons - Shelter Island Farmhouse

Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Peaceful Bright Country House

Centrally located bright, and spacious three-bedroom home 10-minute walk to Crescent Beach and town for shopping and cafes. Nice backyard for barbecue Enjoy a peaceful stay at this quiet and colorful country home on beautiful Shelter Island. 1-minute walk to Léon 1909 restaurant and the Tuck Shop for ice cream. 2-minute drive to historic Goat Hill public golf course. NO PETS PLEASE

Quaint Chalet w/Salt-heated Pool

Our heated pool is open until the beginning of October in 2025. A brand-new two-bedroom chalet that opens onto a heated, saltwater pool directly outside your patio doors. This is your ideal year-around gateway to experience Greenport. This private oasis is walking distance to Greenport Village, 4th & 5th Street beaches, as well as the train station and Jitney stop.

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.