Vacation rentals with a patio in Shelter Island Heights

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in Shelter Island Heights

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Greenport

4.9 out of 5 average rating, 29 reviews

Lovely 1st floor of farmhouse, wineries/downtown

Lovely Victorian home with private entrance, porch, & patio. Floor to ceiling windows in light filled large bedroom with king sized bed & ensuite bathroom. Cozy den has a beautiful bay window and a queen-size pull-out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, and new flat screen TV can be found in the unit. Restaurants, wineries, beaches are nearby. Enjoy all the North Fork as to offer!

Oct. 26 – Nov. 2

$421 CAD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Sep. 18 – 25

$956 CAD per night

Guest favourite

Apartment in Greenport

4.94 out of 5 average rating, 66 reviews

The_BoHo_ Bay_ Stay:apt, 3 blocks from Peconic Bay

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.

Mar. 4 – 11

$731 CAD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 100 reviews

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!

Aug. 10 – 17

$1,360 CAD per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Recently renovated 2-bedroom home directly on the LI Sound. Enjoy fishing on your private beach and sunsets from your private deck. Imagine sipping your morning coffee or afternoon cocktail while listening to the waves crash - it is as if you are sailing at sea! Walking distance to Haylard and the Soundview Hotel, and a 3 minute drive from the town of Greenport. While here, venture to the many acclaimed vineyards or purchase local produce at one of the nearby farmstands!

Oct. 11 – 18

$808 CAD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

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

Close to beaches, wineries, farms, and restaurants--the Salt and Sea House is a relaxing North Fork getaway for vacations and working from home. Uncork a bottle of wine, start up the barbecue, and settle into the beautiful scenery filled with trees and sounds of the sea. Highlights: * 3 min drive to Goose Creek Beach * 4 min drive to Croteaux Vineyards * 7 min drive to Country View farm * Master bath with tub and rain shower * Large fenced in yard * Pack & Play and toys

Jun. 3 – 10

$646 CAD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

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!

Apr. 14 – 21

$682 CAD per night

Guest favourite

Cottage in Shelter Island

4.88 out of 5 average rating, 16 reviews

Waterfront Getaway on Shelter Island

This bright, spacious, private 3 bedroom, 2 bath contemporary home located at the end of the secluded Westmoreland peninsula on Shelter Island is the ideal retreat for summer. Hosting waterfront views from every room leading to a large open deck for gatherings of all kinds. This remote cottage is only 5 minutes from 2 of the best beaches on Shelter Island, Shell and Crescent Beach. Bring your water sports and enjoy Westneck creek and it’s beautiful scenic views!

Nov. 28 – Dec. 5

$1,032 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Nov. 10 – 17

$504 CAD per night

Guest favourite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

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!

Sep. 21 – 28

$600 CAD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 18 reviews

Walk to Beach or to Town …

Situated off a quiet lane, this stylish ,updated residence offers a peaceful and quiet North Fork getaway with 3 well appointed bedrooms 2 .5 modern bathrooms.. Mature landscaping and comfortable outdoor furniture offers a relaxing escape for family & friends. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Nov. 16 – 23

$587 CAD per night

Guest favourite

Apartment in Greenport

4.96 out of 5 average rating, 47 reviews

Newly Renovated 2-BR Apartment

Our quaint apartment is located in the heart of Greenport, it is walking distance to anything you'll need (2 blocks to be exact). The eat-in kitchen has everything you'll need to have a nice home meal. The balcony has comfortable furniture to enjoy a cup of coffee in the morning. We use a August Smart lock for entry.

Dec. 23 – 30

$546 CAD per night