Stayifyoudare - Vacation Rentals in Island's End Golf & Country Club

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From $1,288

         

9.6 (5 Reviews)

House

Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now

• Air Conditioner
• Parking
• Pool

• New York
• Orient

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From $268

         

|

9.2 (14 Reviews)

Bed & Breakfast

Arbor View House Bed and Breakfast

• Air Conditioner
• Parking
• View

• New York
• East Marion

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From $352

         

10.0

House

325 m² House ∙ 4 bedrooms ∙ 8 guests

• 3500 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $469

         

|

9.2 (15 Reviews)

Bed & Breakfast

Arbor View House B&B

• Air Conditioner
• Parking
• Pool

• New York
• East Marion

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From $638

         

10.0 (27 Reviews)

House

House by the Bay with Large In-ground Pool, Steps from Beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• East Marion

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From $550

         

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New

House

Lagoon Lodge: North Fork,Charming 3Br, Waterfront

• Air Conditioner
• Parking
• Pet Friendly

• New York
• East Marion

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From $281

         

9.0

House

139 m² House ∙ 2 bedrooms ∙ 4 guests

• 1500 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $487

         

10.0 (25 Reviews)

House

Cleves Point Estates Home, Private sandy beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From $306

         

New

Villa

BayFront Cottage

• Air Conditioner
• Parking
• View

• New York
• Orient

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From $390

         

10.0 (23 Reviews)

Cottage

Orient Village — Historic Bayfront Cottage — 2025 Season

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $609

         

10.0 (20 Reviews)

House

Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home

• Air Conditioner
• Parking
• Pool

• New York
• East Marion

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From $1,755

         

10.0 (15 Reviews)

House

North Fork Entertainer's Delight!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $812

         

10.0 (5 Reviews)

House

North Fork Paradise

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $1,034

         

10.0 (4 Reviews)

House

SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From $340

         

|

10.0 (3 Reviews)

House

Quiet 3BR home in East Marion. Private beach access 3 min walk away.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $827

         

9.8 (61 Reviews)

House

Beachfront vacation Dream house in Long Island Sound.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $1,763

         

9.4 (10 Reviews)

House

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $246

         

9.4 (8 Reviews)

House

Dog-Friendly Beachfront Home w/Deck, Free WiFi, Ocean Views, & Wood Fireplace

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $459

         

9.4 (3 Reviews)

House

Quiet Oasis Near Greenport and Safe Harbor Marina with Views of Lavendar Farm

• Air Conditioner
• Parking
• TV

• New York
• East Marion

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From $781

         

9.0 (41 Reviews)

House

Renovated and Spacious Summer Home with Water View on Picturesque Island.

• Air Conditioner
• Parking
• Pet Friendly

• Shelter Island Heights
• Hay Beach

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From $1,910

         

New

House

Private Vineyard Estate in Orient Village w Pool/AC/Walk to Beach & Town

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $363

         

New

House

Beautiful home short walk to the beach, w/outdoor shower, grill & central AC

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $576

         

10.0 (98 Reviews)

House

Charming Country Home sits on a 3-acre property in Bucolic Orient.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $880

         

10.0 (75 Reviews)

House

Lovely North Fork Sea Captain's Home

• Air Conditioner
• Parking
• TV

• New York
• East Marion

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Island's End Golf & Country Club.