Family-friendly holiday rentals in Southold
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Southold
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 Southold family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Wading River
4.96 out of 5 average rating, 488 reviewsYour Zen Retreat
Home in Bridgehampton
5 out of 5 average rating, 32 reviewsA Fall/Winter Escape from the City
Cabin in North Fork
4.86 out of 5 average rating, 97 reviewsBeach & Forest: Cozy Cabin, Hot Tub, Peloton
Home in Southampton
4.9 out of 5 average rating, 93 reviewsSouthampton Dream|Modern 5 beds|Near Watermill
Home in Southampton
5 out of 5 average rating, 11 reviewsHamptons Modern Retreat NEW CONS
Home in North Fork
4.96 out of 5 average rating, 52 reviewsMattituck Dream House - Summer Rental Opportunity
Home in Southampton
4.83 out of 5 average rating, 210 reviewsCozy & Chic Summer Getaway near village/beaches
Home in Westhampton Beach
4.92 out of 5 average rating, 143 reviewsHampton's Haven
Family- and pet-friendly home rentals
Home in East Hampton
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in East Hampton
4.89 out of 5 average rating, 109 reviewsGorgeous East Hampton Getaway
Rental unit in Sag Harbor
4.83 out of 5 average rating, 183 reviewsPet friendly Apt. Plus cabin, EV charger & sauna.
Home in Water Mill
4.91 out of 5 average rating, 106 reviewsPeaceful 1850s barn w/Pool
Home in Southampton
4.94 out of 5 average rating, 270 reviewsSouthampton Village Classic-Summer Special!
Rental unit in Sag Harbor
4.93 out of 5 average rating, 152 reviewsWhaling Captain Pierson's Cottage
Rental unit in Southampton
4.87 out of 5 average rating, 127 reviewsSouthampton Village Studio
Home in North Fork
4.95 out of 5 average rating, 63 reviewsNassau Point, North Fork Home w/ Pool
Family-friendly home rentals with a pool
Home in North Fork
4.98 out of 5 average rating, 43 reviewsPrivate pool/walk to beach; farms/vineyards abound
Home in North Fork
4.88 out of 5 average rating, 17 reviewsEat, Love, Stay, and Swim
Home in East Hampton
5 out of 5 average rating, 33 reviewsStunning Central E. Hampton Home w/ gunite pool.
Home in East Hampton
4.89 out of 5 average rating, 9 reviewsHampton Oasis with private Tennis, Pool, Theater
Home in Southampton
4.97 out of 5 average rating, 58 reviewsRenovated Southampton Shores pool, tennis, beach
Home in Water Mill
4.99 out of 5 average rating, 84 reviewsPristine 5 bedroom Home - South of the Highway
Guest house in Shelter Island
4.96 out of 5 average rating, 115 reviewsWaterfront carriage house studio
Home in Watermill
4.88 out of 5 average rating, 138 reviewsModern House close to the beach
Quick stats about holiday rentals that are family-friendly in Southold
Total rentals
180 properties
Nightly prices starting at
$108 SGD before taxes and fees
Total number of reviews
2.5K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Destinations to explore
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