Shelter Island Vacation Home Rentals(68)
Gorgeous Home in Beach Community with Heated Saltwater Pool
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$5,600 -
$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
Relax In This Spacious, Light-filled Vacation Home In Coveted Silver Beach
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$286 -
$357
per night
1 - 7 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 6
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
Airy + Light Island Retreat, Walk to Sunset Beach
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$3,000 -
$3,500
per week
3 - 7 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 7
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
New to Market - Private Beautiful Home 2 Acres, Large Pool, Walk To Wades Beach
- 4 Bedrooms, Sleeps 9
$3,387 -
$6,496
per week
7 night minimum stay
- 4 BR,
- Sleeps 9
Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 7
$6,450 -
$7,250
per week
14 - 28 night minimum stay
- 4 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
Stylish Shelter Island Home with Pool and Walk to Beach.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$2,380 -
$4,375
per week
7 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
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
Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 9
$500 -
$1,000
per night
3 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 9
Spacious Shelter Island Escape within walking distance to pristine beach
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$2,150 -
$2,550
per week
2 - 7 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 10
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
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
Walk to Sunset Beach: Perfect Family Getaway: Historic Colonial
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$100 -
$350
per night
2 - 3 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 10
Shelter Island Beachfront With Pool Offers Great Value!
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
$3,150 -
$4,200
per week
7 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 8
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
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
Peace and Quiet on Shelter Island
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$1,000
per night
3 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Sun Worshipers Paradise
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 1 BA,
- 1 HF 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
Spectacular architects waterfront greek revival
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 9
- 5 BR,
- 4 BA,
- Sleeps 9
Waterfront Charmer on idyllic Shelter Island for summer rental
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
- 3 BR,
- 3 BA,
- Sleeps 8
Coecles Harbor Ram Island Waterfront Estate
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
43 More choices from HomeAway International Websites
Charming, Renovated Island Cottage
- 2 Bedrooms, Sleeps 6
- 2 BR,
- Sleeps 6
Beautiful, Renovated Summer Home
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$2,002 -
$4,004
per week
7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Tranquil Waterfront Gingerbread Cottage-Don't Miss This One!!!
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$180 -
$450
per night
3 night minimum stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Stylishly Renovated Cottage On 1.5 Acres With Pool
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 5
$3,640 -
$5,040
per week
7 - 31 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 5
Shelter Island Waterfront Beach House - Private Beach Perfect Sunsets
- 3 Bedrooms, Sleeps 8
$12,000
per month
14 night minimum stay
- 3 BR,
- Sleeps 8
Advertisement