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
17–24 Dec
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
12–19 Nov
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
4–11 Feb
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
5–12 Jul
Home in Center Moriches
4.98 out of 5 average rating, 188 reviewsWalk to beach and playground. Outdoor hot tub.
18–25 Dec
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
30 Oct – 6 Nov
Home in Southampton
4.82 out of 5 average rating, 198 reviewsCozy & Chic Summer Getaway near village/beaches
3–10 Feb
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
22–29 Dec
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!
11–18 Oct
Home in Montauk
4.91 out of 5 average rating, 418 reviewsDITCH PLAINS SURF HOUSE
1–8 Dec
Flat in Sag Harbor
4.84 out of 5 average rating, 172 reviewsPet friendly, artists apartment & guest cabin.
25 Oct – 1 Nov
Bungalow in Montauk
4.91 out of 5 average rating, 529 reviewsMontauk Oceanview with Fireplace (2)
1–8 Jan
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
8–15 Apr
Home in Montauk
4.87 out of 5 average rating, 181 reviewsLaid-Back Bungalow. 10 min Walk to Beach & Town!
19–26 Oct
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
24–31 Oct
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
23–30 Oct
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
3–10 Oct
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
4–11 Oct
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
25 Oct – 1 Nov
Cottage in Montauk
4.91 out of 5 average rating, 139 reviewsMontauk Cottage Escape
7–14 Dec
Apartment in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
30 Mar – 6 Apr
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Home in Southampton
4.95 out of 5 average rating, 246 reviewsSouthampton Village Classic Summer Special!
25 Oct – 1 Nov
Home in Southampton
4.88 out of 5 average rating, 193 reviewsSecluded Southampton Luxury Estate. 286
8–15 Oct
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
€ 112 before taxes and fees
Destinations to explore
- New City Holiday rentals
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