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
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Dec 17 – 24
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Nov 12 – 19
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb 4 – 11
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 18 – 25
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
Oct 30 – Nov 6
Home in Southampton
4.82 out of 5 average rating, 198 reviewsCozy & Chic Summer Getaway near village/beaches
Feb 3 – 10
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
Dec 22 – 29
Family- and pet-friendly home rentals
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Oct 11 – 18
Home in Montauk
4.91 out of 5 average rating, 418 reviewsDITCH PLAINS SURF HOUSE
Dec 1 – 8
Apartment in Sag Harbor
4.84 out of 5 average rating, 172 reviewsPet friendly, artists apartment & guest cabin.
Oct 25 – Nov 1
Bungalow in Montauk
4.91 out of 5 average rating, 529 reviewsMontauk Oceanview with Fireplace (2)
Jan 1 – 8
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
Apr 8 – 15
Home in Montauk
4.87 out of 5 average rating, 181 reviewsLaid-Back Bungalow. 10 min Walk to Beach & Town!
Oct 19 – 26
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Oct 24 – 31
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
Family-friendly home rentals with a pool
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
Oct 3 – 10
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
Oct 4 – 11
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct 25 – Nov 1
Cottage in Montauk
4.91 out of 5 average rating, 139 reviewsMontauk Cottage Escape
Dec 7 – 14
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Mar 30 – Apr 6
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Jul 20 – 27
Home in Southampton
4.95 out of 5 average rating, 246 reviewsSouthampton Village Classic Summer Special!
Oct 25 – Nov 1
Home in Southampton
4.88 out of 5 average rating, 193 reviewsSecluded Southampton Luxury Estate. 286
Oct 8 – 15
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
R2,257 ZAR before taxes and fees
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