38+ Vacation Rentals Near Little Bay |
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Stayifyoudare - Vacation Rentals in Little Bay

Property Image From $1,288
         

9.6 (5 Reviews)
House
Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $306
         

New
Villa
BayFront Cottage
  • Air Conditioner
  • Parking
  • View

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Property Image From $649
         

8.0
House
149 m² House ∙ 3 bedrooms ∙ 6 guests
  • 1599 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $390
         

10.0 (23 Reviews)
Cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,755
         

10.0 (15 Reviews)
House
North Fork Entertainer's Delight!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $827
         

9.8 (61 Reviews)
House
Beachfront vacation Dream house in Long Island Sound.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $614
         

9.8 (20 Reviews)
House
The Lane House | Private Beach Escape
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,763
         

9.4 (10 Reviews)
House
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $535
         

9.4 (6 Reviews)
House
Orient Point Cottage with Private Beach
  • Air Conditioner
  • Pool
  • TV

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Property Image From $1,064
         

8.0 (1 Review)
House
Sunny home near private community beach with private pool, pool spa, backyard
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,910
         

New
House
Private Vineyard Estate in Orient Village w Pool/AC/Walk to Beach & Town
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,906
         

New
House
Poolside Orient Pt by the sea
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $768
         

New
House
Serene East End Oasis
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $847
         

9.6 (60 Reviews)
House
Orient Point Waterfront Home – Private Beach & Stunning Views
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,350
         

9.6 (21 Reviews)
House
Orient Point Family Waterfront Home
  • Air Conditioner
  • Parking
  • TV

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Property Image From $576
         

10.0 (98 Reviews)
House
Charming Country Home sits on a 3-acre property in Bucolic Orient.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $971
         

10.0 (21 Reviews)
House
Magnificent Private Orient Beach Front House
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,159
         

10.0 (4 Reviews)
Villa
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,285
         

10.0 (1 Review)
House
Gorgeous North Fork Farmhouse with Private Beach Rights
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,150
         

10.0 (1 Review)
House
Luxurious Brand New Home Steps from Beach, Pool and Family-Friendly Amenities!
  • Air Conditioner
  • Pool
  • TV

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Property Image From $885
         

New
House
Preview listing: One-of-a-kind historic home in Orient with space to spread out
  • Air Conditioner
  • Parking
  • TV

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Property Image From $711
         

New
House
Serene East End Oasis
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,847
         

10.0 (8 Reviews)
Other
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,753
         

10.0 (5 Reviews)
Other
Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen
  • Air Conditioner
  • Parking
  • Pool

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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 Little Bay.

Weather in Little Bay

View the weather forecast for Little Bay before booking your Little Bay Vacation Rentals to confirm your best time to go.

December - February
High 42°F       Low 18°F
March - May
High 65°F       Low 22°F
June - August
High 79°F       Low 56°F
September - November
High 76°F       Low 29°F

Top Attractions Around Little Bay, NY

Stayifyoudare offers a large selection of top attractions around Little Bay. Research things to do on your vacation before you visit Little Bay.


The Hamptons Beaches Orient Beach State Park Bay Street Theatre Kontokosta Winery Rocky Neck State Park Old Hook Mill Sparkling Pointe Pleasure Beach Harvey's Beach 67 Steps Beach LongHouse Reserve Corey Creek Winery Mashomack Preserve North Main Street Historic District Pollock-Krasner House and Study Center Hole-in-the-Wall Beach Amagansett Square Orient Point County Park Beach Bungalow The Old Field Vineyards