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Rentals
The Hamptons
Shelter Island
Shelter Island, NY Vacation & Summer Rentals
76 Results
103 South Midway Rd
Shelter Island
$5,000
(February)
3
BD
2.5
BA
Tennis
Listing by Dering Harbor Real Estate
1 Pandion Rd
Shelter Island
$595,000
(Memorial Day - Labor Day)
6
BD
6+
BA
3.4
ACR
6K
FT
2
Waterfront
Listing by Hedgerow Exclusive Properties
(Undisclosed Address)
Shelter Island
$40,000
(July)
3
BD
3
BA
1
ACR
2.89K
FT
2
Pool
Listing by Saunders & Associates
(Undisclosed Address)
Shelter Island
$54,000
(Memorial Day - Labor Day)
1
BD
1
BA
0.62
ACR
1.33K
FT
2
Listing by Saunders & Associates
(Undisclosed Address)
Shelter Island
$31,000
(October)
5
BD
3.5
BA
1.01
ACR
2.55K
FT
2
Gunite Pool
Listing by Saunders & Associates
(Undisclosed Address)
Shelter Island
$15,000
(August - Labor Day)
4
BD
2.5
BA
0.9
ACR
2.05K
FT
2
Listing by Saunders & Associates
23 Tuthill Dr
Shelter Island
$5,000
(February)
3
BD
3
BA
Gunite Pool
Listing by Dering Harbor Real Estate
(Undisclosed Address)
Shelter Island
$10,000
(June)
4
BD
2.5
BA
0.17
ACR
2.14K
FT
2
Listing by Saunders & Associates
32 Hilo Dr
Shelter Island
$69,000
(August - Labor Day)
4
BD
4.5
BA
1
ACR
2.24K
FT
2
Pool
Listing by Corcoran Group
(Undisclosed Address)
Shelter Island
$15,000
(June)
5
BD
4
BA
0.52
ACR
3.13K
FT
2
Listing by Saunders & Associates
(Undisclosed Address)
Shelter Island
$55,000
(July)
5
BD
4.5
BA
0.85
ACR
4.47K
FT
2
Listing by Saunders & Associates
(Undisclosed Address)
Shelter Island
$69,000
(July)
4
BD
4.5
BA
0.91
ACR
5.12K
FT
2
Gunite Pool
Listing by Saunders & Associates
100 West Neck Rd
Shelter Island
$40,000
(Memorial Day - Labor Day)
3
BD
2
BA
1.5
ACR
Pool
Listing by Griffing & Collins Real Estate
(Undisclosed Address)
Shelter Island
$55,000
(July - Labor Day)
5
BD
4.5
BA
Listing by M Wein Realty Inc.
(Undisclosed Address)
Shelter Island
$25,000
(June)
4
BD
3.5
BA
6.8
ACR
1.73K
FT
2
Gunite Pool
Listing by M Wein Realty Inc.
(Undisclosed Address)
Shelter Island
$100,000
(July)
3
BD
3.5
BA
2.22
ACR
3.03K
FT
2
Waterfront
Listing by M Wein Realty Inc.
(Undisclosed Address)
Shelter Island
$65,000
(Memorial Day - Labor Day)
4
BD
4.5
BA
0.92
ACR
2.45K
FT
2
Pool
Listing by M Wein Realty Inc.
(Undisclosed Address)
Shelter Island
$45,000
(August - Labor Day)
4
BD
4.5
BA
1.8
ACR
3.71K
FT
2
Gunite Pool
Listing by M Wein Realty Inc.
3 Lakeview Dr
Shelter Island
$40,000
(Memorial Day - Labor Day)
4
BD
2
BA
0.55
ACR
1.72K
FT
2
Listing by Daniel Gale Sotheby's International Realty
11 Dickerson Dr
Shelter Island
$8,000
(February)
4
BD
4.5
BA
1.3
ACR
3K
FT
2
Gunite Pool
Listing by Dering Harbor Real Estate
5 Bay Ave
Shelter Island
$84,000
(Full Year)
3
BD
3
BA
0.58
ACR
Gunite Pool
Listing by Douglas Elliman Real Estate
8 Petticoat Ln
Shelter Island
$7,500
(June)
3
BD
2.5
BA
Listing by Daniel Gale Sotheby's International Realty
110 South Ferry Rd
Shelter Island
$75,000
(July - Labor Day)
3
BD
3
BA
0.92
ACR
Gunite Pool
Listing by Douglas Elliman Real Estate
104 South Ferry Rd
Shelter Island
$150,000
(Memorial Day - Labor Day)
5
BD
5.5
BA
3.44
ACR
4.04K
FT
2
Gunite Pool
Listing by Daniel Gale Sotheby's International Realty
80 Peconic Ave
Shelter Island
$13,000
(Short-Term)
4
BD
2
BA
0.54
ACR
1.76K
FT
2
Waterfront
Listing by Douglas Elliman Real Estate
2 East Brander Pkwy
Shelter Island
$35,000
(July)
3
BD
3
BA
Waterfront
Listing by Dering Harbor Real Estate
26 Ole Buck Run
Shelter Island
$28,000
(Memorial Day - Labor Day)
3
BD
2
BA
0.89
ACR
1.24K
FT
2
Listing by Daniel Gale Sotheby's International Realty
20 Merkel Ln
Shelter Island
$12,000
(April)
2
BD
2
BA
Waterfront
For Rent By Owner
(Undisclosed Address)
Shelter Island
$18,000
(May)
3
BD
2
BA
0.75
ACR
1.65K
FT
2
Gunite Pool
For Rent By Owner
(Undisclosed Address)
Shelter Island
$55,000
(Memorial Day - Labor Day)
3
BD
2.5
BA
0.68
ACR
2.43K
FT
2
Listing by M Wein Realty Inc.
5 Montclair Ave
Shelter Island
$45,000
(August - Labor Day)
3
BD
1.5
BA
0.5
ACR
1.23K
FT
2
Waterfront
Listing by M Wein Realty Inc.
70 South Ferry Rd
Shelter Island
$4,000
(February)
4
BD
3
BA
Pool
Listing by Marquis New York LLC
6 Cobbetts Ln
Shelter Island
$15,000
(Short-Term)
5
BD
4
BA
Gunite Pool
Listing by Dering Harbor Real Estate
(Undisclosed Address)
Shelter Island
$120,000
(August - Labor Day)
6
BD
4.5
BA
2
ACR
4.24K
FT
2
Waterfront
Listing by M Wein Realty Inc.
13 Winthrop Rd
Shelter Island
$12,000
(Short-Term)
2
BD
2
BA
Pool
Listing by Douglas Elliman Real Estate
12 North Cartwright Rd
Shelter Island
$3,000
(February)
2
BD
1
BA
0.53
ACR
Listing by Griffing & Collins Real Estate
31 Saint Marys Rd
Shelter Island
$50,000
(Memorial Day - Labor Day)
2
BD
1.5
BA
0.62
ACR
1.2K
FT
2
Listing by The Agency
1 Gazon Rd
Shelter Island
$72,000
(Full Year)
4
BD
3
BA
0.5
ACR
2.6
FT
2
Listing by Griffing & Collins Real Estate
32 Saint Marys Rd
Shelter Island
$58,000
(Memorial Day - Labor Day)
3
BD
2.5
BA
0.71
ACR
Gunite Pool
Listing by Dering Harbor Real Estate
8 Burns Rd
Shelter Island
$6,500
(February)
3
BD
3
BA
0.32
ACR
Listing by Douglas Elliman Real Estate
28 Gardiners Bay Dr
Shelter Island
$95,000
(July - Labor Day)
3
BD
3
BA
1.87
ACR
Gunite Pool
Listing by Douglas Elliman Real Estate
(Undisclosed Address)
Shelter Island
$8,000
(February)
5
BD
5.5
BA
0.08
ACR
3.87K
FT
2
Gunite Pool
Listing by Rove Travel
91 Shore Rd
Shelter Island
$40,750
(Memorial Day - Labor Day)
3
BD
1.5
BA
Listing by Griffing & Collins Real Estate
23 North Midway Rd
Shelter Island
$4,500
(February)
4
BD
3
BA
Listing by Dering Harbor Real Estate
12 Emerson Ln
Shelter Island
$5,900
(February)
2
BD
2
BA
1.4
ACR
1.5K
FT
2
Listing by Compass
6 Cozy Ln
Shelter Island
$25,000
(June)
3
BD
2
BA
0.64
ACR
1.42K
FT
2
Pool
Listing by Town & Country Real Estate
99 South Midway Rd
Shelter Island
$100,000
(Memorial Day - Labor Day)
4
BD
3
BA
Pool
Listing by Dering Harbor Real Estate
55 Shore Rd
Shelter Island
$25,500
(Extended Season)
6
BD
5.5
BA
Waterfront
Listing by Marquis New York LLC
15 Montclair Ave
Shelter Island
$16,500
(February)
6
BD
4.5
BA
0.65
ACR
6.5K
FT
2
Waterfront
Listing by Corcoran Group
7 White Birch Rd
Shelter Island
$4,500
(February)
4
BD
2
BA
Listing by Dering Harbor Real Estate