Top Winter Vacations - Vacation Rentals in Great South Bay

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From US $1,129

         

10.0 (72 Reviews)

House

Bungalow in Ocean Bay Park Fire Island- short walk to beach and restaurants!

• Air Conditioner
• TV
• View

• Bay Shore
• Ocean Bay Park

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From US $1,547

         

|

9.5 (2 Reviews)

House

Cayuga Street Sunshine Retreat

• Pet Friendly
• View
• Balcony/Terrace

• Bay Shore
• Ocean Bay Park

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From US $131

         

|

9.4 (427 Reviews)

Hotel

Grove Hotel

• Air Conditioner
• Pool
• View

• Sayville
• Cherry Grove

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From US $908

         

9.0 (59 Reviews)

House

Updated home in great location with spacious living & outdoor features

• Air Conditioner
• Pet Friendly
• TV

• Bay Shore
• Ocean Bay Park

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From US $692

         

|

9.5 (2 Reviews)

Apartment

The Surfcomber Unit 1

• Pet Friendly
• TV
• View

• Bay Shore
• Ocean Bay Park

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From US $656

         

9.0 (2 Reviews)

House

Designer home with bikes & full kitchen - 1 minute from beach

• Air Conditioner
• Pet Friendly
• TV

• Bay Shore
• Ocean Bay Park

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From US $1,871

         

|

9.3 (3 Reviews)

House

15 Seneca

• Air Conditioner
• Pet Friendly
• Pool

• Bay Shore
• Ocean Bay Park

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From US $792

         

10.0 (14 Reviews)

House

Beautiful Ocean Park Family Vacation Rental

• Air Conditioner
• TV
• View

• Bay Shore
• Ocean Bay Park

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From US $1,152

         

9.2 (13 Reviews)

House

Beach Paradise- Ocean Bay Park Fire Island Sleeps 10

• Air Conditioner
• TV
• View

• Ocean Beach
• Seaview

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From US $1,675

         

10.0 (1 Review)

Apartment

Ocean Bay Park Multi-Apartment Home with decks & gas grills

• Air Conditioner
• Parking
• Pet Friendly

• Bay Shore
• Ocean Bay Park

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From US $510

         

9.2 (38 Reviews)

Condo

One Bedroom Apt. in Ocean Bay Park with deck & gas grill

• Air Conditioner
• Parking
• Pet Friendly

• Bay Shore
• Ocean Bay Park

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From US $483

         

9.0 (32 Reviews)

Condo

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

• Air Conditioner
• Pet Friendly
• TV

• Bay Shore
• Ocean Bay Park

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From US $696

         

8.6 (32 Reviews)

House

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

• Air Conditioner
• Parking
• Pet Friendly

• Bay Shore
• Ocean Bay Park

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From US $1,231

         

10.0 (71 Reviews)

House

Newly Renovated Luxury Beach House Ocean Bay Park

• Air Conditioner
• TV
• View

• Bay Shore
• Ocean Bay Park

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From US $779

         

10.0 (27 Reviews)

House

Ocean Bay Park Sanctuary - Families Only Please

• Air Conditioner
• Pet Friendly
• TV

• Bay Shore
• Ocean Bay Park

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From US $725

         

10.0 (21 Reviews)

House

Bayfront Fun! - 3 BR and 3 Ensuite Bath with Hot Tub!

• Air Conditioner
• Pet Friendly
• TV

• Sayville
• Cherry Grove

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From US $2,892

         

10.0 (3 Reviews)

House

Fire Island White House - Ocean Bay Park n5 Bedroom Bayview Home - Sleeps 18!

• Air Conditioner
• Pool
• TV

• Bay Shore
• Ocean Bay Park

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From US $819

         

10.0 (3 Reviews)

Boat Rental

Paradise on the Great South Bay

• Air Conditioner
• Pet Friendly
• Security/Safety

• New York
• Fire Island

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From US $3,044

         

10.0 (2 Reviews)

House

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 26, Steps From The Beach

• Air Conditioner
• Pet Friendly
• Pool

• Bay Shore
• Ocean Bay Park

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From US $854

         

10.0 (2 Reviews)

House

Charming 2-Bedroom Beach Cottage in Ocean Bay Park

• Air Conditioner
• TV
• Balcony/Terrace

• Bay Shore
• Ocean Bay Park

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From US $1,095

         

10.0 (1 Review)

House

Ocean Beach 4Bed 2.5Baths Luxury Kitchen Spacious Decks Swim Spa Outdoor Shower

• Air Conditioner
• Pool
• TV

• New York
• Fire Island

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From US $1,642

         

9.8 (9 Reviews)

House

Stunning, light-filled beach house with hot tub & sauna, minutes from the beach!

• Air Conditioner
• Pool
• TV

• New York
• Fire Island

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From US $841

         

9.6 (8 Reviews)

House

Fire Island Beach House

• Air Conditioner
• TV
• View

• Bay Shore
• Ocean Bay Park

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From US $1,119

         

9.4 (23 Reviews)

House

Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

• Air Conditioner
• Pet Friendly
• TV

• Bay Shore
• Ocean Bay Park

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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 Great South Bay.