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
Home in North Fork
4.97 out of 5 average rating, 203 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in North Fork
4.94 out of 5 average rating, 17 reviewsChic Beach House: Waterfront, Vineyards, Hot Tub
Home in East Hampton
4.94 out of 5 average rating, 72 reviewsFamily Friendly Springs Beach House
Cottage in Southampton
4.96 out of 5 average rating, 177 reviewsSecluded Southampton Cottage w/Pool & Spa
Cabin in North Fork
4.86 out of 5 average rating, 98 reviewsBeach & Forest: Cozy Cabin, Hot Tub, Peloton
Home in Shelter Island
4.88 out of 5 average rating, 24 reviewsNEWLY RENOVATED W/ POOL & FIREPLACE
Home in Bayport
4.83 out of 5 average rating, 161 reviewsExquisite spacious waterfront all modern-sleeps 8
Home in Southampton
4.83 out of 5 average rating, 210 reviewsCozy & Chic Summer Getaway near village/beaches
Family- and pet-friendly home rentals
Cottage in North Fork
4.97 out of 5 average rating, 150 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Home in East Hampton
4.88 out of 5 average rating, 110 reviewsGorgeous East Hampton Getaway
Home in Sag Harbor
4.85 out of 5 average rating, 159 reviewsSag Harbor House for rent.
Home in North Fork
4.98 out of 5 average rating, 244 reviewsThe Greenport Bungalow
Apartment in Sag Harbor
4.83 out of 5 average rating, 184 reviewsPet friendly Apt. Plus cabin, EV charger & sauna.
Guest suite in North Fork
4.92 out of 5 average rating, 155 reviewsGREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
Home in North Fork
4.91 out of 5 average rating, 101 reviewsNorth Fork Escape - Walk To Village, Beach, Parks
Cottage in Port Jefferson Station
4.8 out of 5 average rating, 433 reviewsThe Red Cottage Circa 1936
Family-friendly home rentals with a pool
Home in North Fork
4.88 out of 5 average rating, 123 reviewsThe Perfect North Fork Escape
Home in Hampton Bays
4.94 out of 5 average rating, 122 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in Sag Harbor
4.82 out of 5 average rating, 136 reviewsThanksgiving! Sag Harbor Gem!
Home in East Hampton
4.88 out of 5 average rating, 109 reviewsModern East Hampton Home w/ Heated Saltwater Pool
Home in East Hampton
4.74 out of 5 average rating, 89 reviewsClean Home Pool Cent-Loc. Quiet Reserve Pet Friend
Home in East Hampton
5 out of 5 average rating, 35 reviewsStunning Central E. Hampton Home w/ gunite pool.
Home in East Hampton
4.94 out of 5 average rating, 157 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Sag Harbor
4.85 out of 5 average rating, 261 reviewsExclusive Sag Harbor Compound
Quick stats about vacation rentals that are family-friendly in Southold
Total rentals
180 properties
Nightly prices starting at
G$16,719 GYD 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
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