Beach Home Rentals in Shelter Island Whale's Tail, NY: Compare 10+ Sites & Save

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40 Beach Home Rentals in Shelter Island Whale's Tail (Starting from $318)

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
0.4k from Shelter Island Whale's Tail 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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Peaceful and Private Shelter Island Getaway
Peaceful and Private Shelter Island Getaway
House
Shelter Island, NY, 11964, United States
0.7k from Shelter Island Whale's Tail 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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Charming, Historic Cottage
Charming, Historic Cottage
Cottage
Shelter Island, NY, 11964, United States
0.7k from Shelter Island Whale's Tail 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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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
1.1k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$318
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
1.2k from Shelter Island Whale's Tail 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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Private oasis with new baths and heated Gunite pool near Wades Beach
Private oasis with new baths and heated Gunite pool near Wades Beach
House
Shelter Island, NY, 11964, United States
1.3k from Shelter Island Whale's Tail center

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

4 Bedrooms8 Guests
10.0

Exceptional

33 reviews

$961
Average price / night
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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
1.7k from Shelter Island Whale's Tail center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$504
Average price / night
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Relax By The Pool, Or Walk To The Beach And Restaurants
Relax By The Pool, Or Walk To The Beach And Restaurants
House
Shelter Island Heights, NY, 11965, United States
1.7k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$710
Average price / night
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Hilltop Cottage Privacy Abounds
Hilltop Cottage Privacy Abounds
House
Shelter Island, NY, 11964, United States
1.7k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
7.4

Good

3 reviews

$599
Average price / night
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Shelter Island Sun Filled Modern Waterfront Home with Dock
Shelter Island Sun Filled Modern Waterfront Home with Dock
House
Shelter Island, NY, 11964, United States
1.8k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$411
Average price / night
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 Perfect Family Summer Vacation Home Close to beach 18x42 pool
Perfect Family Summer Vacation Home Close to beach 18x42 pool
House
Shelter Island, NY, 11964, United States
1.9k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
9.6

Exceptional

54 reviews

$756
Average price / night
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
House
Shelter Island, NY, 11964, United States
2.0k from Shelter Island Whale's Tail center

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

4 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$942
Average price / night
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Classic Waterview Victorian Summer Cottage in Park-Like-Setting
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
House
Shelter Island Heights, NY, 11965, United States
2.1k from Shelter Island Whale's Tail center

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

5 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$688
Average price / night
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Kick back and unwind
Kick back and unwind
House
Shelter Island Heights, NY, 11965, United States
2.1k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$556
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
2.2k from Shelter Island Whale's Tail 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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Spacious 5-bedroom house in delightful Shelter Island
Spacious 5-bedroom house in delightful Shelter Island
House
Shelter Island, NY, 11964, United States
2.2k from Shelter Island Whale's Tail center

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

5 Bedrooms10 Guests
New to Booking
$656
Average price / night
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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
House
Shelter Island, NY, 11964, United States
2.2k from Shelter Island Whale's Tail center

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

4 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$1035
Average price / night
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Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
House
Shelter Island Heights, NY, 11965, United States
2.2k from Shelter Island Whale's Tail center

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

4 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$1001
Average price / night
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Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
House
Shelter Island Heights, NY, 11965, United States
2.2k from Shelter Island Whale's Tail center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1123
Average price / night
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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
2.2k from Shelter Island Whale's Tail 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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Charming Studio on Shelter Island
Charming Studio on Shelter Island
Apartment
Shelter Island, NY, 11964, United States
2.2k from Shelter Island Whale's Tail center

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

1 Bedroom2 Guests
New to Booking
$371
Average price / night
Check Availability
Spacious Modern on wooded lot - 5 min from beach!
Spacious Modern on wooded lot - 5 min from beach!
House
Shelter Island, NY, 11964, United States
2.2k from Shelter Island Whale's Tail center

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

4 Bedrooms8 Guests
New to Booking
$793
Average price / night
Check Availability
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
2.3k from Shelter Island Whale's Tail 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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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
2.3k from Shelter Island Whale's Tail center

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

4 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$773
Average price / night
Check Availability
Lovely home by the sea with dock and heated Gunite pool!
Lovely home by the sea with dock and heated Gunite pool!
House
Shelter Island, NY, 11964, United States
2.3k from Shelter Island Whale's Tail center

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

4 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$579
Average price / night
Check Availability
 Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
House
Shelter Island Heights, NY, 11964, United States
2.3k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
9.4

Superb

6 reviews

$931
Average price / night
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Newly renovated! Shelter Island Gem,  3 blocks from Sunset Beach
Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
House
Shelter Island Heights, NY, 11968, United States
2.4k from Shelter Island Whale's Tail center

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

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$1079
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 Beach Rentals in Shelter Island Whale's Tail.

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Shelter Island Whale's Tail Beach Rentals on the Map

Frequently Asked Questions

You can explore 40 verified beach rentals in Shelter Island Whale's Tail. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Shelter Island Whale's Tail vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $318 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Shelter Island Whale's Tail offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Shelter Island Whale's Tail welcome pets. Currently, 21 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Shelter Island Whale's Tail often include amenities designed for coastal living, such as Bedding/Linens, View, and Ocean View. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.