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Luxury Houses for Rent in Shelter Island, NY

25 rentals

4 Ivy Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

SINGLE_FAMILY - Contemporary - Shelter Island, NY

4 Ivy Pl, Shelter Island, NY 11964

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$63,000

House for rent

Top amenities
Furnished
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
28 Gardiners Bay Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

Single Family Residence, Contemporary - Shelter Island, NY

28 Gardiners Bay Drive, Shelter Island, NY 11964

Luxury | Swimming pool | In-unit laundry

3 beds

3 baths

$50,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
28 Windermere Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

28 Windermere Dr, Sag Harbor, NY 11963

Luxury | Swimming pool | Fireplace

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

Luxury | Roof deck | Swimming pool

3 beds

2 baths

$45,000

House for rent

Top amenities
On-Site Laundry
Swimming Pool
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

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$40,000

House for rent

Top amenities
Furnished
Storage
Swimming Pool
28 Dartmouth Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

28 Dartmouth Rd, Sag Harbor, NY 11963

Luxury | Balcony | Swimming pool

5 beds

6 baths

$100,000

House for rent

Top amenities
Garage Parking
Swimming Pool

Nearby rental good for eco-living

$40,000

Sag Harbor

Nearby rental good for social life

23 Marjorie Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

23 Marjorie Ln, Sag Harbor, NY 11963

Luxury | Outdoor space | Garage parking

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

Luxury | Swimming pool | Outdoor space

5 beds

6 baths

$25,000

House for rent

Top amenities
Swimming Pool
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310 Old Shipyard Ln - Photo 1 of 1

3d ago

Luxury house for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

310 Old Shipyard Ln, Southold, NY 11971

Luxury | In-unit laundry | Dishwasher

3 beds

1 bath

$4,000

House for rent

Top amenities
In-Unit Laundry
1110 Gillette Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in East Marion

SINGLE_FAMILY - Cape Cod - East Marion, NY

1110 Gillette Dr, East Marion, NY 11939

Luxury | In-unit laundry | Hardwood floor

4 beds

2 baths

$7,000

House for rent

Top amenities
In-Unit Laundry
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Find sweet deals near Shelter Island

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

$25,000

Sag Harbor

$3,500

Southold

$25,000

Southold

$10,000

Greenport

42 North Menantic Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

Residential, Contemporary - Shelter Island, NY

42 North Menantic Road, Shelter Island, NY 11964

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$7,500

House for rent

Top amenities
Air Conditioning
Dishwasher
Fireplace
Hardwood Floor
In-Unit Laundry
Swimming Pool
380 Ed's Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Other - Southold, NY

380 Ed's Road, Southold, NY 11971

Luxury | In-unit laundry | Outdoor space

4 beds

2 baths

$3,600

House for rent

Top amenities
Hardwood Floor
In-Unit Laundry
1000 Rambler Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Colonial - Southold, NY

1000 Rambler Road, Southold, NY 11971

Luxury | Balcony | Walk-in closets

4 beds

3 baths

$50,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
425 Cedar Point Drive East - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Contemporary, Mediterranean, Modern - Southold, NY

425 Cedar Point Drive East, Southold, NY 11971

Luxury | Walk-in closets | Swimming pool

5 beds

3 baths

$25,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
517 Flint Street - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

SINGLE_FAMILY - Bungalow - Greenport, NY

517 Flint Street, Greenport, NY 11944

Luxury | In-unit laundry | Outdoor space

2 beds

1 bath

$4,000

House for rent

Top amenities
In-Unit Laundry
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

Luxury | Roof deck | Walk-in closets

3 beds

3 baths

$90,000

House for rent

Top amenities
Fireplace
On-Site Laundry
Residents Lounge
Roof Deck
2524 Noyac Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2524 Noyac Rd, Sag Harbor, NY 11963

Luxury | Swimming pool | On-site laundry

7 beds

9 baths

$15,000

House for rent

Top amenities
Fireplace
On-Site Laundry
4315 Noyac Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

4315 Noyac Rd, Sag Harbor, NY 11963

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$4,500

House for rent

Top amenities
In-Unit Laundry
Swimming Pool
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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

Luxury | Swimming pool | Outdoor space

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

Luxury | Swimming pool | Outdoor space

4 beds

3 baths

$70,000

House for rent

Top amenities
Garage Parking
21 Bull Run - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

21 Bull Run, East Hampton, NY 11937

Luxury | Swimming pool | Garage parking

5 beds

6 baths

$70,000

House for rent

Top amenities
Garage Parking
3825 S Harbor Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence, Ranch - Southold, NY

3825 S Harbor Rd, Southold, NY 11971

Luxury | In-unit laundry | Hardwood floor

2 beds

1 bath

$3,500

House for rent

Top amenities
Furnished
In-Unit Laundry
5125 Main Bayview Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

5125 Main Bayview Rd, Southold, NY 11971

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$4,000

House for rent

Top amenities
Carpet
Dishwasher
Hardwood Floor
In-Unit Laundry
110 Sleepy Hollow Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Colonial - Southold, NY

110 Sleepy Hollow Ln, Southold, NY 11971

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$30,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
Swimming Pool
2421 Noyac Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Sag Harbor

Exp Ranch, Single Family Residence - Sag Harbor, NY

2421 Noyac Rd, Sag Harbor, NY 11963

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$55,000

House for rent

Top amenities
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Shelter Island > Shelter Island Luxury Houses For Rent
Updated: December 26, 2025

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