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
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
17–24 Oct
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
21–26 Jul
Guest suite in Patchogue
4.93 out of 5 average rating, 268 reviewsShores Retreat Suite - Peaceful Relaxation
21–28 Jul
Home in Southampton
4.82 out of 5 average rating, 199 reviewsCozy & Chic Summer Getaway near village/beaches
30 May – 6 Jun
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
20–27 Dec
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
24 Sep – 1 Oct
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
30 Oct – 6 Nov
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
16–23 Nov
Family- and pet-friendly home rentals
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
14–21 Feb
Flat in Hampton Bays
4.97 out of 5 average rating, 340 reviewsPrivate & Cozy Cottage with short walk to beach!
5–12 Apr
Home in East Hampton
4.95 out of 5 average rating, 191 reviewsRex- East Hampton Cottage- 5 stars
17–24 Sep
Home in East Hampton
4.94 out of 5 average rating, 202 reviewsPrivate beach Historical House with large property
16–23 Mar
Home in Southampton
4.87 out of 5 average rating, 237 reviewsSecluded Southampton Luxury Estate with tennis 288
24–31 Dec
Flat in Southampton
4.86 out of 5 average rating, 107 reviewsSouthampton Village Studio
28 Mar – 4 Apr
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
2–9 Dec
Cottage in Guilford
4.93 out of 5 average rating, 245 reviewsCharm + location. Walk to beach, town, & harbor.
8–15 Oct
Family-friendly home rentals with a pool
Guest house in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
13–20 Oct
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
7–14 Aug
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
10–17 Oct
Home in Watermill
4.88 out of 5 average rating, 128 reviewsModern House close to the beach
19–26 Dec
Home in Southampton
4.95 out of 5 average rating, 247 reviewsSouthampton Village Classic
20–27 Sep
Home in Cutchogue
4.94 out of 5 average rating, 50 reviewsNassau Point, North Fork Home w/ Pool
14–21 Oct
Home in Cutchogue
4.97 out of 5 average rating, 36 reviewsPrivate pool/walk to beach; farms/vineyards abound
24–31 Mar
Home in East Hampton
4.96 out of 5 average rating, 55 reviewsEast Hampton Family Vacation Home
19–26 Feb
Quick stats about holiday 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
2T reviews
Nightly prices starting at
₹8,341 before taxes and fees
Destinations to explore
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- Rentals with a patio Southold
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- Family-friendly rentals Southold
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