Beachfront vacation rentals in Southold
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Southold
Guests agree: these beachfront 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 beachfront rentals
Pet-friendly beachfront home rentals
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Nov 30 – Dec 7
Apartment in Sag Harbor
4.98 out of 5 average rating, 117 reviewsSag Harbor Retreat
May 28 – Jun 4
Home in Greenport
5.0 out of 5 average rating, 19 reviewsWalk to Beach or to Town …
Nov 16 – 23
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
Dec 13 – 20
Home in Old Saybrook
4.98 out of 5 average rating, 48 reviewsSteps to Beach! *Cozy Cottage* Pet Friendly
Oct 27 – Nov 3
Home in New Suffolk
5.0 out of 5 average rating, 11 reviewsWaterfront Beach Cottage
Sep 19 – 26
Home in Greenport
4.9 out of 5 average rating, 20 reviewsmodern 3 bedroom home with fireplace
Dec 17 – 24
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Nov 27 – Dec 4
Beachfront home rentals with a pool
Home in New London
4.89 out of 5 average rating, 131 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Oct 20 – 27
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Oct 23 – 30
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Jan 7 – 14
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
Jun 12 – 19
Villa in Greenport
4.84 out of 5 average rating, 32 reviewsYear-Round Heated Pool Villa - 3 blocks from town
Mar 10 – 17
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
Apr 7 – 14
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
Jan 11 – 18
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
Apr 9 – 16
Private beachfront home rentals
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun 11 – 18
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Oct 13 – 20
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Dec 6 – 13
Apartment in Greenport
4.96 out of 5 average rating, 24 reviewsVintage 1880 Victorian gem.
Nov 6 – 13
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
Jan 17 – 24
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Nov 18 – 25
Home in Peconic
5.0 out of 5 average rating, 11 reviewsCoastal Cottage on the Water
Oct 4 – 11
Apartment in Greenport
4.78 out of 5 average rating, 46 reviews2 Bedroom Greenport Waterfront Coastal Cottage
Apr 9 – 16
Quick stats about beachfront rentals in Southold
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
470 reviews
Nightly prices starting at
G$23,012 GYD before taxes and fees
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