Family-friendly vacation 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.
Vacation 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
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Apr 26 – May 3
Cottage in Southampton
4.96 out of 5 average rating, 164 reviewsSecluded Southampton Cottage w/Pool & Spa
Oct 9 – 16
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Oct 20 – 27
Guest suite in Patchogue
4.93 out of 5 average rating, 268 reviewsShores Retreat Suite - Peaceful Relaxation
Jun 21 – 26
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
Aug 19 – 26
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
Nov 3 – 10
Home in Southampton
4.82 out of 5 average rating, 199 reviewsCozy & Chic Summer Getaway near village/beaches
Jun 4 – 11
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
Oct 30 – Nov 6
Family- and pet-friendly home rentals
Apartment in Hampton Bays
4.97 out of 5 average rating, 340 reviewsPrivate & Cozy Cottage with short walk to beach!
Sep 20 – 27
Home in East Hampton
4.95 out of 5 average rating, 191 reviewsRex- East Hampton Cottage- 5 stars
Oct 25 – Nov 1
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
Sep 16 – 23
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Oct 28 – Nov 4
Home in East Hampton
4.94 out of 5 average rating, 203 reviewsPrivate beach Historical House with large property
Aug 25 – Sep 1
Cottage in Guilford
4.93 out of 5 average rating, 245 reviewsCharm + location. Walk to beach, town, & harbor.
Oct 2 – 9
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
Oct 10 – 17
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
Oct 10 – 17
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct 25 – Nov 1
Home in Watermill
4.88 out of 5 average rating, 128 reviewsModern House close to the beach
Oct 16 – 23
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 8 – 15
Home in Southampton
4.95 out of 5 average rating, 247 reviewsSouthampton Village Classic
Nov 30 – Dec 7
Home in Southampton
4.78 out of 5 average rating, 147 reviewsSecluded Southampton Get-Away. “290”
May 30 – Jun 6
Home in Cutchogue
4.94 out of 5 average rating, 50 reviewsNassau Point, North Fork Home w/ Pool
Feb 4 – 11
Home in Cutchogue
4.97 out of 5 average rating, 36 reviewsPrivate pool/walk to beach; farms/vineyards abound
Jan 10 – 17
Quick stats about vacation rentals that are family-friendly in Southold
Total rentals
190 properties
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
70 properties allow pets
Total number of reviews
2K reviews
Nightly prices starting at
$100 before taxes and fees
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