House vacation rentals in Shelter Island
Find and book unique houses on Airbnb
Top-rated house rentals in Shelter Island
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island house rentals
House rentals with a hot tub
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Dec 4 – 11
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Nov 11 – 18
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Jan 8 – 15
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
Jul 5 – 12
Home in Center Moriches
4.98 out of 5 average rating, 188 reviewsWalk to beach and playground. Outdoor hot tub.
Dec 1 – 8
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
Oct 30 – Nov 6
Home in Shirley
4.98 out of 5 average rating, 202 reviewsBy NYC & Hamptons - Hot Tub, Pool Table, Speakeasy
Sep 10 – 17
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
Dec 17 – 24
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Nov 26 – Dec 3
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Oct 23 – 30
Home in Water Mill
4.91 out of 5 average rating, 109 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Nov 15 – 22
Home in Sag Harbor
4.81 out of 5 average rating, 108 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Jun 6 – 13
Home in Cutchogue
4.87 out of 5 average rating, 115 reviewsThe Perfect North Fork Escape
Sep 29 – Oct 6
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Dec 29 – Jan 5
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Oct 27 – Nov 3
House rentals with free parking
Home in East Hampton
4.94 out of 5 average rating, 202 reviewsPrivate beach Historical House with large property
Jun 10 – 17
Home in Greenport
4.92 out of 5 average rating, 121 reviewsBeautiful Cottage Home W/ Beach & Dock Access
Jun 6 – 13
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
May 12 – 19
Home in Southold
5.0 out of 5 average rating, 15 reviewsLe Petit Cottage Southold NY
Apr 8 – 15
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Oct 13 – 20
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
May 3 – 10
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Jan 6 – 13
Home in Sag Harbor
5.0 out of 5 average rating, 92 reviewsSecluded Modern Beach Style House
Sep 24 – Oct 1
Quick stats about house rentals in Shelter Island
Total rentals
100 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
$120 before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Martha's Vineyard Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Lakehouse rentals New York
- Guesthouse rentals New York
- Townhouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Beach house rentals New York
- Earth house rentals United States
- Guesthouse rentals United States
- House rentals United States
- Townhouse rentals United States
- Lighthouse rentals United States
- Townhouse rentals Manhattan
- Guesthouse rentals Manhattan
- House rentals Manhattan
- House rentals Brooklyn
- Townhouse rentals Brooklyn
- Guesthouse rentals Brooklyn
- Guesthouse rentals New York
- Townhouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Treehouse rentals New York
- Fitness-friendly rentals Shelter Island
- Rentals with a washer and dryer Shelter Island
- Rentals with a patio Shelter Island
- Rentals with pools Shelter Island
- Rentals with a fireplace Shelter Island
- Family-friendly rentals Shelter Island
- Kid-friendly rentals Shelter Island
- Monthly Rentals Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with a fire pit Shelter Island
- Beachfront rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with outdoor seating Shelter Island
- Tiny house rentals Suffolk County
- Guesthouse rentals Suffolk County
- House rentals Suffolk County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes