Waterfront holiday rentals in Southold
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Top-rated waterfront rentals in Southold
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for waterfront rentals in Southold
Waterfront apartment rentals
Flat in Sag Harbor
4.98 out of 5 average rating, 117 reviewsSag Harbor Retreat
16–23 May
Flat in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
8–15 Jun
Flat in Branford
4.89 out of 5 average rating, 9 reviewsStony Crk Studio ideal for trvl nurses…
4–11 Mar
Flat in East Haven
4.97 out of 5 average rating, 66 reviewsCoastal Relaxation Getaway
18–25 Nov
Flat in Branford
4.93 out of 5 average rating, 15 reviewsOcean front 1 bedroom apartment
9–16 Mar
Flat in Greenport
4.79 out of 5 average rating, 281 reviewsAmazing Greenport Village Apartment in CENTER!
25 Nov – 2 Dec
Flat in Greenport
5.0 out of 5 average rating, 3 reviewsHarborview King with Balcony at Greenport
13–20 Aug
Flat in West Haven
4.67 out of 5 average rating, 114 reviewsHome on the sound
6–13 Dec
Waterfront house rentals
Home in Milford
4.89 out of 5 average rating, 124 reviewsThe Beach House!
5–12 May
Home in New Haven
4.97 out of 5 average rating, 125 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
27 Sep – 4 Oct
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
16–23 Jan
Home in Shirley
4.98 out of 5 average rating, 179 reviewsLuxurious Waterfront Beachouse On The Bay ~
13–20 Mar
Home in East Patchogue
4.82 out of 5 average rating, 132 reviewsHouse at water next to Bellport golf course
22–29 Mar
Home in Southold
4.79 out of 5 average rating, 14 reviewsNorth Fork Lakefront cottage near Kenney's beach
3–10 Aug
Home in East Marion
4.87 out of 5 average rating, 15 reviewsWaterfront NoFo Cottage w/ public beach access
16–23 May
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
13–20 Sep
Waterfront apartment rentals
Apartment in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
25 Sep – 2 Oct
Apartment in Shelter Island Heights
5.0 out of 5 average rating, 5 reviewsPeaceful and Relaxing Waterfront.
4–11 Apr
Apartment in Greenport
4.87 out of 5 average rating, 90 reviewsWaterfront Condo C-204 at The Cliffside Resort
23–30 Jun
Apartment in Old Lyme
4.38 out of 5 average rating, 8 reviewsHawks Nest Condo style unit on the sand!
23–30 Apr
Apartment in Greenport
Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
11–18 Dec
Apartment in Greenport
4.83 out of 5 average rating, 100 reviewsSeaside Escape w Pool, Private Beach + Patio
19–26 Dec
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
₹8,341 before taxes and fees
Destinations to explore
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- Rentals with a patio Southold
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