Oceanfront Rentals in The Heights, NY: Compare 10+ Sites & Save

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177 Best Oceanfront Rentals in The Heights (Starting from $236)

Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
2.8k from The Heights 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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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
0.4k from The Heights 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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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
3.5k from The Heights 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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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
0.5k from The Heights 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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Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
4.6k from The Heights 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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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
0.5k from The Heights 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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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
6.5k from The Heights 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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Shore House - A Luxury Beach Retreat
Shore House - A Luxury Beach Retreat
House
Shelter Island Heights, NY, 11965, United States
0.5k from The Heights center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$3370
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
7.3k from The Heights 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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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
0.6k from The Heights 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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Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
7.6k from The Heights center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$391
Average price / night
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Kick back and unwind
Kick back and unwind
House
Shelter Island Heights, NY, 11965, United States
0.6k from The Heights 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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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
7.6k from The Heights center

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

1 Bedroom8 Guests
New to Booking
$499
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
0.7k from The Heights 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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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
9.8k from The Heights 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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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
1.0k from The Heights 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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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
1.0k from The Heights center

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

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$1079
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
1.4k from The Heights 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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 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
1.5k from The Heights 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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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
1.7k from The Heights 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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Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Apartment
Greenport, NY, 11944, United States
1.8k from The Heights center

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

2 Bedrooms4 Guests
10.0

Exceptional

150 reviews

$518
Average price / night
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Haven on Glynn by Rove Travel | 3BR Coastal Luxury
Haven on Glynn by Rove Travel | 3BR Coastal Luxury
House
Shelter Island, NY, 11964, United States
1.9k from The Heights center

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

3 Bedrooms8 Guests
New to Booking
$1067
Average price / night
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Old meets new in this fully renovated 19th century farm house.
Old meets new in this fully renovated 19th century farm house.
House
Greenport, NY, 11944, United States
2.0k from The Heights center

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

2 Bedrooms5 Guests
10.0

Exceptional

8 reviews

$511
Average price / night
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Cottage on Beach front Estate with Dockage  .Walk to Village
Cottage on Beach front Estate with Dockage .Walk to Village
Cottage
greenport, NY, 11944, United States
2.0k from The Heights center

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

3 Bedrooms4 Guests
9.8

Exceptional

80 reviews

$359
Average price / night
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Fishermans Cottage near Crescent Beach
Fishermans Cottage near Crescent Beach
House
Shelter Island, NY, 11965, United States
2.0k from The Heights center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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Walk to Beach and Greenport Village, Two King Beds
Walk to Beach and Greenport Village, Two King Beds
House
Greenport, NY, 11944, United States
2.0k from The Heights center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$630
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
2.0k from The Heights center

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

6 Bedrooms16 Guests
New to Booking
$1723
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 The Heights.

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The Heights Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 177 verified oceanfront rentals in The Heights. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in The Heights 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 The Heights 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 The Heights welcome pets. Currently, 24 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 The Heights 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.