
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

Private Oasis W/Stunning Vinyard and Pool Views

Greenport Village walking distance to all

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

1800 Historical EH Home, 1 Mile to Town, Hot Tub!
Family- and pet-friendly home rentals

Corwin House

PICTURE PERFECT SOUTHAMPTON HOME-

Savor Ocean Sunsets at a Soothing Beachfront Haven

Waterfront NoFo Cottage w/ public beach access

Gorgeous home with saltwater pool. Steps to beach!

Elegant Modern Artist's Residence

Cozy Farmhouse Retreat in North Fork, NY

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
Family-friendly home rentals with a pool

Hamptons Home w/ Salt Water Pool

Spectacular Southampton Retreat!

East Hampton 3 Bed / 3 Bath Charmer w Pool

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Beautiful Waterview Condo on the North Fork of LI

Classic Southampton Village Home w/ Pool

B our guest! King bed 2 bths Fireplace convenient

Beachside Waterview 2Br Condo w/ Pool in Greenport
Quick stats about vacation rentals that are family-friendly in Shelter Island
Total rentals
120 properties
Nightly prices starting at
€ 103 before taxes and fees
Total number of reviews
2.1K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Rentals with pools Shelter Island
- Pet-friendly rentals Shelter Island
- Fitness-friendly rentals Shelter Island
- Beachfront rentals Shelter Island
- Rentals with a fireplace Shelter Island
- Rentals with outdoor seating Shelter Island
- Waterfront rentals Shelter Island
- Rentals with a washer and dryer Shelter Island
- Rentals with a patio Shelter Island
- Rentals with a fire pit Shelter Island
- House rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a kayak Shelter Island
- Family-friendly rentals Suffolk County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park