Kid-friendly holiday rentals in Shelter Island
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Shelter Island
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in Greenport
4.98 out of 5 average rating, 143 reviewsGreenport Village walking distance to all
10–17 May
Home in Sag Harbor
4.95 out of 5 average rating, 129 reviewsLuxury Private King Suite + 2 Floor Living Space
25 Dec – 1 Jan
Home in Greenport
4.92 out of 5 average rating, 121 reviewsBeautiful Cottage Home W/ Beach & Dock Access
31 May – 7 Jun
Home in East Hampton
4.95 out of 5 average rating, 191 reviewsRex- East Hampton Cottage- 5 stars
3–10 Sep
Home in Sag Harbor
4.97 out of 5 average rating, 124 reviewsRelax into Coastal Life at a Sun-Drenched Sag Harbor Home
24 Nov – 1 Dec
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
29 Dec – 5 Jan
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
12–19 May
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
28 Oct – 4 Nov
Family-friendly apartment rentals
Flat in Southold
4.96 out of 5 average rating, 100 reviewsBright, Southold Studio Apt near beach & town
30 May – 6 Jun
Flat in New London
4.98 out of 5 average rating, 289 reviewsQuiet Neighborhood home close to everything
9–16 Oct
Flat in Sag Harbor
4.98 out of 5 average rating, 117 reviewsSag Harbor Retreat
5–12 Jan
Flat in Greenport
4.86 out of 5 average rating, 141 reviewsQuiet Neighborhood and only steps to Town
14–21 Dec
Flat in Sag Harbor
4.92 out of 5 average rating, 133 reviewsWhaling Captain Pierson's Apartment TOO
3–10 Jun
Flat in Rocky Point
4.93 out of 5 average rating, 123 reviewsNorth shore Guest Room.
3–8 Jun
Flat in Sag Harbor
4.84 out of 5 average rating, 172 reviewsPet friendly, artists apartment & guest cabin.
25 Oct – 1 Nov
Flat in Sag Harbor
4.88 out of 5 average rating, 133 reviewsSag Harbor Village Oasis
13–20 Dec
Family-friendly apartment rentals
Apartment in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
8–15 Oct
Apartment in Greenport
4.93 out of 5 average rating, 124 reviewsBeautiful Waterview Condo on the North Fork of LI
10–17 Nov
Apartment in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
9–16 Oct
Apartment in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
30 Mar – 6 Apr
Apartment in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
13–20 Sep
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
26 Oct – 2 Nov
Apartment in Sag Harbor
4.86 out of 5 average rating, 43 reviewsCute cottage apartment upstairs above store in Sag
2–9 May
Quick stats about holiday rentals that are kid-friendly in Shelter Island
Total rentals
20 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
730 reviews
Nightly prices starting at
€ 187 before taxes and fees
Destinations to explore
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- Family-friendly rentals Shelter Island
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