Family-friendly vacation rentals in Shelter Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shelter Island
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Sag Harbor
4.82 out of 5 average rating, 133 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Home in North Fork
4.96 out of 5 average rating, 192 reviewsPrivate Oasis Stunning Views 7/6 - 7/20 Available
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
Home in Wading River
4.96 out of 5 average rating, 466 reviewsYour Zen Retreat
Cottage in North Fork
4.69 out of 5 average rating, 188 reviewsLovely 2 BR Beach House No. Shore
Home in Westhampton Beach
4.93 out of 5 average rating, 139 reviewsHampton's Haven
Home in Southampton
4.83 out of 5 average rating, 201 reviewsCozy & Chic Summer Getaway near village/beaches
Home in Shelter Island
4.89 out of 5 average rating, 71 reviewsCedar Home Cottage on Shelter Island
Family- and pet-friendly home rentals
Guest suite in North Fork
4.94 out of 5 average rating, 142 reviewsGREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
Rental unit in Sag Harbor
4.84 out of 5 average rating, 172 reviewsPet friendly apartment & cabin with sauna.
Home in East Hampton
4.94 out of 5 average rating, 198 reviewsRex- East Hampton Cottage- 5 stars
Cottage in North Fork
4.97 out of 5 average rating, 130 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Home in East Hampton
4.93 out of 5 average rating, 148 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in East Hampton
4.92 out of 5 average rating, 131 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.87 out of 5 average rating, 190 reviewsHeated Salt Water Pool, Walk 2 Beach, Fence 4 Pup
Home in East Haven
4.88 out of 5 average rating, 201 reviewsBeach Cottage by the Sea
Family-friendly home rentals with a pool
Guest suite in East Hampton
4.89 out of 5 average rating, 226 reviewsPrivate Cozy Cottage with Pool / Private Beach
Home in Watermill
4.88 out of 5 average rating, 130 reviewsModern House close to the beach
Home in North Fork
4.87 out of 5 average rating, 118 reviewsThe Perfect North Fork Escape
Home in Southampton
4.95 out of 5 average rating, 133 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Cottage in Montauk
4.92 out of 5 average rating, 145 reviewsMontauk Cottage Escape
Condo in Montauk
4.95 out of 5 average rating, 111 reviewsDeluxe Studio Apt@The Montauk Manor
Condo in Montauk
4.8 out of 5 average rating, 233 reviewsMontauk Royal Atlantic Beach Resort North
Home in Southampton
4.94 out of 5 average rating, 252 reviewsSouthampton Village Classic
Quick stats about vacation rentals that are family-friendly in Shelter Island
Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
50 properties allow pets
Total number of reviews
1.8K reviews
Nightly prices starting at
$120 before taxes and fees
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- Monthly Rentals Shelter Island
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