Oceanfront Rentals in Shelter Island, NY: Compare 10+ Sites & Save

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270 Best Oceanfront Rentals in Shelter Island (Starting from $236)

Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
3.5k from Shelter Island center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
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Waterfront House With Dock And Private Beach
Waterfront House With Dock And Private Beach
House
Shelter Island, NY, 11964, United States
0.7k from Shelter Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$740
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
6.4k from Shelter Island center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$972
Average price / night
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Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
7.0k from Shelter Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
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WATERFRONT with Private Beach Boat Dock and Launch Ramp
WATERFRONT with Private Beach Boat Dock and Launch Ramp
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1060
Average price / night
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queeen room
queeen room
House
Shelter Island, New York, USA
7.3k from Shelter Island center

Internet, Oceanfront, Balcony/Terrace, View, Ocean View, Air Conditioner, Private Beach

1 Bedroom3 Guests
9.0

Fabulous

1 reviews

$270
Average price / night
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Work and Play Special!  Extended Stay Discount
Work and Play Special! Extended Stay Discount
House
Shelter Island, NY, 11964, United States
1.1k from Shelter Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
10.0

Exceptional

53 reviews

$1308
Average price / night
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Villa KeyLime
Villa KeyLime
Villa
Sag Harbor, NY, USA
7.4k from Shelter Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

5 Bedrooms9 Guests
New to Booking
$1241
Average price / night
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Private wooded summer house 5 minute walk to Wades Beach
Private wooded summer house 5 minute walk to Wades Beach
House
Shelter Island, NY, 11964, United States
1.5k from Shelter Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$773
Average price / night
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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
7.8k from Shelter Island center

Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
Average price / night
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Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
House
Shelter Island, NY, 11964, United States
2.1k from Shelter Island center

AC, Dryer, Free Parking, Heater, Kitchen, No Smoking, Patio, Pool, TV

3 Bedrooms6 Guests
New to Booking
$997
Average price / night
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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
8.3k from Shelter Island center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
New to Booking
$500
Average price / night
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Charming, Historic Cottage
Charming, Historic Cottage
Cottage
Shelter Island, NY, 11964, United States
2.2k from Shelter Island center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$752
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
9.0k from Shelter Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

3 Bedrooms6 Guests
New to Booking
$811
Average price / night
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Private Sag Harbor estate on expansive property with sprawling manicured lawns
Private Sag Harbor estate on expansive property with sprawling manicured lawns
House
Sag Harbor, NY, 11963, United States
2.6k from Shelter Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

6 Bedrooms14 Guests
New to Booking
$4341
Average price / night
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Recently Renovated, Inviting Home in Quiet Location
Recently Renovated, Inviting Home in Quiet Location
House
Shelter Island, New York, USA
9.2k from Shelter Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$950
Average price / night
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Chic Coastal Farmhouse with Private Pool, Steps from the Water Your...
Chic Coastal Farmhouse with Private Pool, Steps from the Water Your...
House
Shelter Island, NY, 11964, United States
2.8k from Shelter Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$1851
Average price / night
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Cowgirl Palace
Cowgirl Palace
House
Sag Harbor, NY, USA
9.3k from Shelter Island center

Accommodations, Pools, Parking, Homestays, Lodgings, Vacation rentals, Jacuzzis, Places to stay, Family

6 Bedrooms18 Guests
5.9

Review score

19 reviews

$950
Average price / night
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Peaceful and Private Shelter Island Getaway
Peaceful and Private Shelter Island Getaway
House
Shelter Island, NY, 11964, United States
2.8k from Shelter Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms5 Guests
10.0

Exceptional

52 reviews

$402
Average price / night
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Shelter Island Retreat, 5 bdrms near everything!
Shelter Island Retreat, 5 bdrms near everything!
House
Shelter Island, NY, 11964, United States
2.9k from Shelter Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$834
Average price / night
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 Ideal for 2 families, private,  pool, close to beaches and marina  Sleeps 12
Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12
House
Shelter Island, NY, 11964, United States
2.9k from Shelter Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1042
Average price / night
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NEW RENTAL:  MAGICAL SHELTER ISLAND RETREAT
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
House
Shelter Island, NY, 11964, United States
3.0k from Shelter Island center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$2378
Average price / night
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Charming Studio on Shelter Island
Charming Studio on Shelter Island
Apartment
Shelter Island, NY, 11964, United States
3.0k from Shelter Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
New to Booking
$371
Average price / night
Check Availability
Waterfront Victorian farmhouse with heated pool and deepwater dock
Waterfront Victorian farmhouse with heated pool and deepwater dock
House
Shelter Island, NY, 11964, United States
3.2k from Shelter Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms16 Guests
New to Booking
$1723
Average price / night
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Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
House
Shelter Island, NY, 11964, United States
3.3k from Shelter Island center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
9.6

Exceptional

13 reviews

$1116
Average price / night
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Relaxing Shelter Island Getaway - great for families and couples!
Relaxing Shelter Island Getaway - great for families and couples!
House
Shelter Island Heights, NY, 11965, United States
3.3k from Shelter Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$318
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Shelter Island.

Where to stay in Shelter Island? Best neighborhoods & areas

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Shelter Island Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 270 verified oceanfront rentals in Shelter Island. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Shelter Island vary depending on the property size, exact beachfront location, and season. Rates typically start from around $236 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Shelter Island offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Shelter Island welcome pets. Currently, 25 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Shelter Island often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.