Family-friendly holiday 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.
Holiday 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
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsPrivate Oasis W/Stunning Vinyard And Pool Views
Home in Westhampton Beach
4.93 out of 5 average rating, 136 reviewsHampton's Haven
Home in Wading River
4.97 out of 5 average rating, 461 reviewsYour Zen Retreat
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
Home in Southampton
4.82 out of 5 average rating, 199 reviewsCozy & Chic Summer Getaway near village/beaches
Home in Shelter Island
4.89 out of 5 average rating, 70 reviewsCedar Home Cottage on Shelter Island
Home in Sag Harbor
4.95 out of 5 average rating, 84 reviewsSag village, 4 en-suite BRs, hot tub, beach 5 mins
Family- and pet-friendly home rentals
Home in East Hampton
4.92 out of 5 average rating, 130 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.95 out of 5 average rating, 194 reviewsRex- East Hampton Cottage- 5 stars
Guest suite in Greenport
4.94 out of 5 average rating, 142 reviewsGREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
Home in East Hampton
4.94 out of 5 average rating, 204 reviewsPrivate beach Historical House with large property
Flat in Sag Harbor
4.84 out of 5 average rating, 172 reviewsPet friendly artists apartment & cabin with sauna
Home in Montauk
4.91 out of 5 average rating, 421 reviewsDITCH PLAINS SURF HOUSE
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
Bungalow in Montauk
4.91 out of 5 average rating, 534 reviewsMontauk Oceanview with Fireplace (2)
Family-friendly home rentals with a pool
Guest suite in East Hampton
4.89 out of 5 average rating, 223 reviewsPrivate Cozy Cottage with Pool / Private Beach
Home in Hampton Bays
4.98 out of 5 average rating, 113 reviewsBeach House Feel - newly renovated backyard Oasis
Home in Southampton
4.95 out of 5 average rating, 132 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Home in Watermill
4.88 out of 5 average rating, 128 reviewsModern House close to the beach
Cottage in Montauk
4.92 out of 5 average rating, 142 reviewsMontauk Cottage Escape
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Apartment in Montauk
4.95 out of 5 average rating, 110 reviewsDeluxe Studio Apt@The Montauk Manor
Quick stats about holiday 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
€ 111 before taxes and fees
Destinations to explore
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- Pet-friendly rentals Shelter Island
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