Beachfront holiday houses in Southold
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Top-rated beachfront accommodation in Southold
Guests agree: These beachfront 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 beachfront rentals
Pet-friendly beachfront home rentals
Apartment in Sag Harbor
4.98 out of 5 average rating, 117 reviewsSag Harbor Retreat
16 – 23 May
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
30 Nov – 7 Dec
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
24 – 31 Dec
Home in Old Saybrook
4.96 out of 5 average rating, 49 reviewsSteps to Beach! *Cozy Cottage* Pet Friendly
13 – 20 Apr
Home in Greenport
4.95 out of 5 average rating, 20 reviewsWalk to Beach or to Town …
16 – 23 Nov
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
6 – 13 Jan
Home in Greenport
4.9 out of 5 average rating, 20 reviewsmodern 3 bedroom home with fireplace
19 – 26 Dec
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
12 – 19 May
Beachfront home rentals with a pool
Condo in Greenport
4.89 out of 5 average rating, 81 reviewsSeaside Escape w Pool, Private Beach & Patio
4 – 11 Dec
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
25 Sept – 2 Oct
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
8 – 15 June
Villa in Greenport
4.84 out of 5 average rating, 32 reviewsYear-Round Heated Pool Villa - 3 blocks from town
17 – 24 Feb
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
28 Feb – 7 Mar
Home in Southampton
5.0 out of 5 average rating, 18 reviewsBeautiful Southampton Home w/ Pool, Close to Beach
5 – 12 Jan
Home in Hampton Bays
4.89 out of 5 average rating, 45 reviewsHamptons Round Beach House - 60 secs walk to beach
14 – 21 Apr
Home in Hampton Bays
5.0 out of 5 average rating, 37 reviews4 BR Hamptons Oasis w/ Private Pool & Beach Access
28 Nov – 5 Dec
Private beachfront home rentals
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
15 – 22 Oct
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
11 – 18 June
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
8 – 15 Dec
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
9 – 16 Dec
Home in Southold
4.97 out of 5 average rating, 78 reviewsSouthold Beach house.
13 – 20 May
Home in Peconic
5.0 out of 5 average rating, 11 reviewsCoastal Cottage on the Water
4 – 11 Oct
Cottage in Cutchogue
5.0 out of 5 average rating, 50 reviewsThe Melody Too
28 Nov – 5 Dec
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
12 – 19 Apr
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
$168 AUD before taxes and fees
Destinations to explore
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- Rentals with a kayak Southold
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