Waterfront vacation rentals in Southold
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Southold
Guests agree: these waterfront rentals 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 waterfront rentals
Waterfront apartment rentals
Apartment in New Haven
4.89 out of 5 average rating, 467 reviewsFair Haven Heights Entire 1 Bedroom Apartment
Oct 9 – 16
Apartment in Sag Harbor
4.98 out of 5 average rating, 117 reviewsSag Harbor Retreat
May 28 – Jun 4
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
Jun 12 – 19
Apartment in Branford
4.89 out of 5 average rating, 9 reviewsStony Crk Studio ideal for trvl nurses…
Dec 20 – 27
Apartment in East Haven
4.97 out of 5 average rating, 66 reviewsCoastal Relaxation Getaway
Nov 16 – 23
Apartment in Milford
5.0 out of 5 average rating, 49 reviewsThe Pond Mill Retreat w/ 2 Bdrms & Pool
Oct 13 – 20
Apartment in Branford
4.93 out of 5 average rating, 15 reviewsOcean front 1 bedroom apartment
Apr 4 – 11
Apartment in Milford
4.96 out of 5 average rating, 49 reviewsSteps to the Beach. Lovely 2-Bedroom apt
Mar 14 – 21
Waterfront house rentals
Home in East Lyme
4.96 out of 5 average rating, 164 reviewsBeachfront Paradise
Apr 26 – May 3
Home in Milford
4.89 out of 5 average rating, 124 reviewsThe Beach House!
May 2 – 9
Home in New Haven
4.97 out of 5 average rating, 125 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
Aug 23 – 30
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Jan 14 – 21
Home in Shirley
4.98 out of 5 average rating, 178 reviewsLuxurious Waterfront Beachouse On The Bay ~
Mar 21 – 28
Home in Southold
4.79 out of 5 average rating, 14 reviewsNorth Fork Lakefront cottage near Kenney's beach
Jul 16 – 23
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Feb 18 – 25
Home in Peconic
5.0 out of 5 average rating, 11 reviewsCoastal Cottage on the Water
Oct 4 – 11
Waterfront condo rentals
Condo in Greenport
4.89 out of 5 average rating, 81 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
Condo in New Haven
4.89 out of 5 average rating, 18 reviewsLuxurious 1B, high-ceiling loft in New Haven.
Nov 16 – 23
Condo in Shelter Island Heights
5.0 out of 5 average rating, 5 reviewsPeaceful and Relaxing Waterfront.
Apr 2 – 9
Condo in Greenport
4.87 out of 5 average rating, 90 reviewsWaterfront Condo C-204 at The Cliffside Resort
May 30 – Jun 6
Condo in Old Lyme
4.38 out of 5 average rating, 8 reviewsHawks Nest Condo style unit on the sand!
Oct 21 – 28
Condo in Greenport
Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
Dec 11 – 18
Condo in Greenport
4.83 out of 5 average rating, 100 reviewsSeaside Escape w Pool, Private Beach + Patio
Feb 10 – 17
Quick stats about waterfront rentals in Southold
Total rentals
50 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
560 reviews
Nightly prices starting at
R1,879 ZAR before taxes and fees
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