Shelter Island with Outdoor Grill(84)
Gorgeous Home in Beach Community with Heated Saltwater Pool
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$5,950
per week
7 - 31 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
Romantic Waterfront Hideaway
- 4 Bedrooms,
- 7 Bathrooms, Sleeps 14
$5,500
per week
7 night Minimum Stay
- 4 BR,
- 7 BA,
- Sleeps 14
Contemporary Home With Old Vocabulary In Walking Distance To Beaches
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$6,000 -
$11,000
per month
28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
Airy + Light Island Retreat, Walk to Sunset Beach
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$500
per night
3 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$11,029 -
$19,375
per month
14 - 31 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 6
Relax In This Spacious, Light-filled Vacation Home In Coveted Silver Beach
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$286
per night
1 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
New to Market - Private Beautiful Home 2 Acres, Large Pool, Walk To Wades Beach
- 4 Bedrooms, Sleeps 10
$15,000 -
$25,000
per month
14 night Minimum Stay
- 4 BR,
- Sleeps 10
Luxury,Quiet, Pool,Spotless, Beach,Main+Guest House,June Still Avail!
- 6 Bedrooms,
- 7 Bathrooms, Sleeps 14
$5,000 -
$7,395
per week
2 - 7 night Minimum Stay
- 6 BR,
- 7 BA,
- Sleeps 14
Contemporary luxury home with pool in the Heights
- 4 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 8
$1,000 -
$3,000
per night
3 night Minimum Stay
- 4 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 8
Design and Comfort Come Together in this Island Beach Home
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$2,800 -
$4,750
per week
7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
Eclectic Round House- 4 Bedroom+Cottage+Pool on 1.5 Priv Acres
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 7
$10,000
per week
7 - 28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 7
Spacious Shelter Island Escape within walking distance to pristine beach
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$2,150 -
$2,550
per week
2 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 10
Nature Lover's Delight!
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$3,500 -
$5,425
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
ROMANTIC Hamptons Beach Cottage! Seclusion, Waterfalls
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$335 -
$495
per night
2 - 7 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 9
$1,000
per night
3 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 9
Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$400 -
$695
per night
3 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Adorable Waterfront Cottage
- 2 Bedrooms,
- 1 Bathroom, Sleeps 6
- 2 BR,
- 1 BA,
- Sleeps 6
Stylish Shelter Island Home with Pool and Walk to Beach.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Tranquil Island Refuge Nestled Among Towering Trees and Near Private Beach
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$1,900 -
$2,575
per week
3 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Charming Cottage. June available. Can rent year around.
- 3 Bedrooms,
- 1 Bathroom, Sleeps 3
$5,002 -
$5,075
per month
29 night Minimum Stay
- 3 BR,
- 1 BA,
- Sleeps 3
Walk to Sunset Beach: Perfect Family Getaway: Historic Colonial
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$200 -
$350
per night
2 - 3 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 10
Rustic house w/ pool on 2 private acres
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$8,000 -
$15,000
per month
3 - 28 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Very elegant, with hot tub, large deck and lush landscape
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
$3,500
per week
2 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 8
Charming Water View Victorian ' Eden Roc ' in Park-like-Setting
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 6
$30,000 -
$35,000
per month
7 night Minimum Stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 6
Breathtaking & Charming Shelter Island Oasis 5BR 3.5BA on Private Acre
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$5,000 -
$7,000
per week
28 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Waterfront Charmer on idyllic Shelter Island for summer rental
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
- 3 BR,
- 3 BA,
- Sleeps 8
Spectacular architects waterfront greek revival
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 9
- 5 BR,
- 4 BA,
- Sleeps 9
Sun Worshipers Paradise
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Relax by the Pool at This Comfortable 3 Bedroom Retreat
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 3 BR,
- 2 BA,
- Sleeps 8
Advertisement