Zumper

Houses for Rent in Shelter Island, NY

Average rent

$25,000

Track prices

Rent calculator

What can I afford?

All rentals

42 North Menantic Road - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

Residential, Contemporary - Shelter Island, NY

42 North Menantic Road, Shelter Island, NY 11964

In-unit laundry | Garage parking | Air conditioning

4 beds

2 baths

$7,500

House for rent

Modern Mid-Century Retreat with Heated Pool

This beautifully renovated 4-bedroom, 2.5-bath home offers a stunning blend of mid-century style and modern comfort, spanning 2,800 sq ft. Enjoy seamless indoor-outdoor living with five sliding glass doors leading to a heated gunite pool and expansive deck. The gourmet kitchen features a granite island and Electrolux appliances, while the lower level includes a kitchenette and recreational space. Ideal for relaxation or entertaining, this retreat is just moments from beaches and local dining on Shelter Island.

4 Ivy Pl - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

SINGLE_FAMILY - Contemporary - Shelter Island, NY

4 Ivy Pl, Shelter Island, NY 11964

In-unit laundry | Garage parking | High ceilings

3 beds

2 baths

$63,000

House for rent

Charming Contemporary Retreat with Spacious Loft

This delightful 3-bedroom, 2-bath home in Hay Beach offers a perfect blend of comfort and style. A large living room with a cozy fireplace opens to an awning-covered deck, ideal for relaxation. The spacious loft provides a versatile space for an office or guest overflow, while the fully furnished interior ensures ease and convenience. Enjoy the tranquil surroundings just minutes from Gardiners Bay Country Club in this charming contemporary sanctuary, spanning 1,487 square feet.

15 Montclair Ave - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

Single Family Residence - Shelter Island, NY

15 Montclair Ave, Shelter Island, NY 11964

Swimming pool | Hardwood floor | Walk-in closets

6 beds

4 baths

$75,000

House for rent

Luxurious Waterfront Oasis with Private Dock

Nestled in West Neck Harbor, this 4,600 sq ft waterfront home features a private dock with a boat and captain, a designer interior, and breathtaking harbor views. Enjoy a first-floor primary suite, an adjacent guest cottage, and luxurious outdoor living with a heated saltwater pool, spa, sauna, and sunset-facing deck. This masterfully designed retreat offers six bedrooms, three living spaces, and a seamless blend of elegance and leisure.

15 S Cartwright Rd - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

Single Family Residence, Mid-century Modern - Shelter Island, NY

15 S Cartwright Rd, Shelter Island, NY 11964

In-unit laundry | Garage parking | Swimming pool

4 beds

4 baths

$30,000

House for rent

Stylishly Renovated Home with Heated Pool Retreat

This stunning 4-bedroom, 4-bath home spans 3,100 sq ft and features a modern open-plan great room that seamlessly connects to the pool and expansive fenced garden. Enjoy the beautifully landscaped grounds from the rock garden patio and relax in the 20x40 heated pool. Conveniently located within walking distance to beaches and local cafe, it perfectly combines comfort with the allure of Shelter Island living.

18 Xxxxxx Dickerson Drive - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

Single Family Residence, Colonial - Shelter Island, NY

18 Xxxxxx Dickerson Drive, Shelter Island, NY 11964

In-unit laundry | Garage parking | Swimming pool

4 beds

3 baths

$40,000

House for rent

Stunning Renovated Retreat with Heated Pool

This immaculate 4-bedroom, 3.5-bathroom home boasts over 2,700 sq ft of exquisite living space, perfect for tranquil getaways. Recently renovated and beautifully furnished, the property features a brand new heated gunite pool, set in one of the quietest neighborhoods. Enjoy the stunning design and tasteful decor that make this rental a magnificent choice for relaxation and entertainment. A true escape not to be missed!

28 Gardiners Bay Drive - Photo 1 of 1

5d+ ago

House for rent in Shelter Island

Single Family Residence, Contemporary - Shelter Island, NY

28 Gardiners Bay Drive, Shelter Island, NY 11964

In-unit laundry | Garage parking | Swimming pool

3 beds

3 baths

$50,000

House for rent

Tranquil Waterfront Escape with Infinity Pool

Enjoy breathtaking panoramic water views and mesmerizing sunrises over Gardiner's Bay from every room in this luxurious 3,000 sq ft contemporary retreat. Featuring open-plan living spaces, a chef's kitchen, and an oversized primary suite with private deck. The outdoors delights with a waterside infinity pool, dining pavilion, and professionally landscaped gardens, making this an unforgettable waterfront sanctuary.

Nearby rental good for eco-living

Nearby rental good for social life

28 Windermere Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

28 Windermere Dr, Sag Harbor, NY 11963

Swimming pool | Fireplace | Residents lounge

4 beds

3 baths

$45,000

House for rent

30 Sunset Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

30 Sunset Rd, Sag Harbor, NY 11963

On-site laundry | Outdoor space | Swimming pool

3 beds

2 baths

$45,000

House for rent

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
68 W Water St ##Unit - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

68 W Water St ##Unit, Sag Harbor, NY 11963

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$40,000

House for rent

28 Dartmouth Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

28 Dartmouth Rd, Sag Harbor, NY 11963

Outdoor space | Garage parking | Swimming pool

5 beds

6 baths

$100,000

House for rent

Advertisement

Find sweet deals near Shelter Island

These rentals are 10%-30% cheaper than the local average price for similar rentals.

23 Marjorie Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

23 Marjorie Ln, Sag Harbor, NY 11963

Outdoor space | Garage parking | Fireplace

2 beds

2 baths

$30,000

House for rent

156 Main St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

156 Main St, Sag Harbor, NY 11963

Outdoor space | Swimming pool | Fireplace

5 beds

6 baths

$25,000

House for rent

310 Old Shipyard Ln - Photo 1 of 1

3d ago

House for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

310 Old Shipyard Ln, Southold, NY 11971

In-unit laundry | Dishwasher

3 beds

1 bath

$4,000

House for rent

1110 Gillette Dr - Photo 1 of 1

5d+ ago

House for rent in East Marion

SINGLE_FAMILY - Cape Cod - East Marion, NY

1110 Gillette Dr, East Marion, NY 11939

In-unit laundry | Hardwood floor | Dishwasher

4 beds

2 baths

$7,000

House for rent

380 Ed's Road - Photo 1 of 1

5d+ ago

House for rent in Southold

SINGLE_FAMILY - Other - Southold, NY

380 Ed's Road, Southold, NY 11971

In-unit laundry | Outdoor space | Hardwood floor

4 beds

2 baths

$3,600

House for rent

1000 Rambler Road - Photo 1 of 1

5d+ ago

House for rent in Southold

SINGLE_FAMILY - Colonial - Southold, NY

1000 Rambler Road, Southold, NY 11971

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$50,000

House for rent

Listings within 10 miles
10 Quadrant Hill Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

10 Quadrant Hill Rd, East Hampton, NY 11937

On-site laundry | Outdoor space | Swimming pool

3 beds

3 baths

$90,000

House for rent

2524 Noyac Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2524 Noyac Rd, Sag Harbor, NY 11963

On-site laundry | Garage parking | Swimming pool

7 beds

9 baths

$15,000

House for rent

4315 Noyac Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

4315 Noyac Rd, Sag Harbor, NY 11963

In-unit laundry | Swimming pool | Fireplace

3 beds

2 baths

$4,500

House for rent

Advertisement
11 N Cape Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

11 N Cape Ln, East Hampton, NY 11937

Outdoor space | Swimming pool | Fireplace

4 beds

2 baths

$15,000

House for rent

643 Stephen Hands Path - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

643 Stephen Hands Path, East Hampton, NY 11937

Outdoor space | Garage parking | Swimming pool

4 beds

3 baths

$70,000

House for rent

21 Bull Run - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

21 Bull Run, East Hampton, NY 11937

Garage parking | Swimming pool | High ceilings

5 beds

6 baths

$70,000

House for rent

3825 S Harbor Rd - Photo 1 of 1

5d+ ago

House for rent in Southold

Single Family Residence, Ranch - Southold, NY

3825 S Harbor Rd, Southold, NY 11971

In-unit laundry | Hardwood floor | Furnished

2 beds

1 bath

$3,500

House for rent

5125 Main Bayview Rd - Photo 1 of 1

5d+ ago

House for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

5125 Main Bayview Rd, Southold, NY 11971

In-unit laundry | Garage parking | Carpet

3 beds

2 baths

$4,000

House for rent

110 Sleepy Hollow Ln - Photo 1 of 1

5d+ ago

House for rent in Southold

SINGLE_FAMILY - Colonial - Southold, NY

110 Sleepy Hollow Ln, Southold, NY 11971

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$30,000

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Shelter Island
Updated: December 26, 2025

Are you a rental professional?

Try our tenant screening, or post rental listings to Zumper, Craigslist Shelter Island, and more.

Discover houses for rent in Shelter Island, NY

🌇Available house rentals25 houses
💰Best rent deal380 Ed's Road
Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos