Vacation Rentals in Southold, NY
PRICE PER NIGHT
ACCOMMODATION TYPES
Water View Beach House just steps to Private Sandy Beach!
No reviews
·
Southold
·
4 br
·
Sleeps 10
·
Hot Tub · Waterfront · Fitness Center ·
From
$698/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Waterfront
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Kitchen
The Shoals Suites & Slips
9.4
Excellent
·
Southold
·
1 br
·
Sleeps 4
·
Assigned Parking · Free Parking · Balcony ·
From
$428/nightProperty
Hotel · 1 Bed · 1 bath
Amenities
Assigned Parking
Free Parking
Fireplace
Wifi
Air Conditioning
Furnished
Business Center
Concierge Service
Other spaces
Balcony, Kitchen
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
10
Excellent
·
Southold
·
3 br
·
Sleeps 6
·
Hardwood Floor · Lake · Waterfront ·
From
$454/nightProperty
House · 3 Beds · 2 baths
Amenities
Hardwood Floor
Lake
Waterfront
Fitness Center
Beach
Fireplace
Oven
Dishwasher
Other spaces
Workspace, Kitchen
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
9.3
Excellent
·
Southold
·
3 br
·
Sleeps 7
·
Ceiling Fan · Workspace · Beach ·
From
$589/nightProperty
House · 3 Beds · 2 baths
Amenities
Ceiling Fan
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Piece of Paradise in the Middle of LI Wine Country
No reviews
·
Southold
·
4 br
·
Sleeps 12
·
Balcony · Private Pool · Pool ·
From
$398/nightProperty
House · 4 Beds · 4 baths
Amenities
Private Pool
Pool
Beach
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Sunny and quiet home - steps from the bay!
No reviews
·
Southold
·
3 br
·
Sleeps 6
·
Workspace · Fireplace · Dishwasher ·
From
$575/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Beautifully appointed waterfront property with heated pool and cabana
9.6
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
Private Pool · Waterfront · Pool ·
From
$1,083/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Waterfront
Pool
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Walk to beach! Simple Cottage Bliss. Peaceful & Private.
10
Excellent
·
Southold
·
2 br
·
Sleeps 4
·
On Site Laundry · Ceiling Fan · Fitness Center ·
From
$224/nightProperty
House · 2 Beds · 2 baths
Amenities
On Site Laundry
Ceiling Fan
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Workspace, Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
5BR Beach House, In Ground Heated Pool, Walk to Private Beach! Close to all!
10
Excellent
·
Southold
·
6 br
·
Sleeps 10
·
On Site Laundry · Deck · Balcony ·
From
$900/nightProperty
House · 6 Beds · 3 baths
Amenities
On Site Laundry
Private Pool
Pool
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Deck, Balcony, Workspace, Kitchen
**Location** HEATED SALTWATER Pool Walk to Sandy Beach, Town, Restaurants, Shops
No reviews
·
Southold
·
5 br
·
Sleeps 12
·
Ski In Ski Out · Private Pool · Pool ·
From
$815/nightProperty
House · 5 Beds · 4 baths
Amenities
Ski In Ski Out
Private Pool
Pool
Fitness Center
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Kitchen
Entertainers Delight Just Steps From The Beach
9.9
Excellent
·
Southold
·
4 br
·
Sleeps 14
·
Private Pool · Pool · Fireplace ·
From
$200/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Sweet Southold Beach Cottage WINTER/SPRING/SUMMER/SEASONAL
7
Very good
·
Southold
·
2 br
·
Sleeps 2
·
On Site Laundry · Ceiling Fan · Fitness Center ·
From
$148/nightProperty
House · 2 Beds · 1 bath
Amenities
On Site Laundry
Ceiling Fan
Fitness Center
Beach
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Kitchen
Heated Saltwater Pool | Private Escape | Near Beach & Wineries
No reviews
·
Southold
·
4 br
·
Sleeps 10
·
High Ceilings · Walk In Closets · Private Pool ·
From
$665/nightProperty
House · 4 Beds · 3 baths
Amenities
High Ceilings
Walk In Closets
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Workspace, Kitchen
Privacy!! Heated salt-water pool, central a/c, all kinds of families welcome
No reviews
·
Southold
·
3 br
·
Sleeps 8
·
Balcony · Private Pool · Pool ·
From
$649/nightProperty
House · 3 Beds · 3 baths
Amenities
Private Pool
Pool
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
North Fork Sound Front Beach House
9.5
Excellent
·
Southold
·
4 br
·
Sleeps 6
·
Central Heat · Ocean · Waterfront ·
From
$636/nightProperty
House · 4 Beds · 2 baths
Amenities
Central Heat
Ocean
Waterfront
Fitness Center
Beach
Fireplace
Oven
Dishwasher
Other spaces
Kitchen
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
10
Excellent
·
Southold
·
2 br
·
Sleeps 6
·
Fitness Center · Beach · Outdoor Space ·
From
$339/nightProperty
House · 2 Beds · 2 baths
Amenities
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Bayfront Vacation Home in Southold, 5 Bedrooms
10
Excellent
·
Southold
·
5 br
·
Sleeps 8
·
Smoking Allowed · Balcony · Waterfront ·
From
$711/nightProperty
House · 5 Beds · 4 baths
Amenities
Smoking Allowed
Waterfront
Fitness Center
Beach
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Unique Southold waterfront luxury home with heated pool on Long Creek
9.5
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
Ev Charging · Ceiling Fan · Balcony ·
From
$1,148/nightProperty
House · 4 Beds · 4 baths
Amenities
Ev Charging
Ceiling Fan
Waterfront
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Charming house walking distance from beautiful Kenney’s Beach
10
Excellent
·
Southold
·
2 br
·
Sleeps 4
·
Workspace · Beach · Outdoor Space ·
From
$276/nightProperty
House · 2 Beds · 1 bath
Amenities
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Walk to beach & vineyard from this brand new home
No reviews
·
Southold
·
3 br
·
Sleeps 6
·
Workspace · Outdoor Space · Fireplace ·
From
$513/nightProperty
House · 3 Beds · 3 baths
Amenities
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Located on a sandy dune in Southold
9.9
Excellent
·
Southold
·
3 br
·
Sleeps 8
·
Waterfront · Beach · Oven ·
From
$1,064/nightProperty
Apartment · 3 Beds · 4 baths
Amenities
Waterfront
Beach
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
2 Bedroom Apartment in Historic Home with private yard (WBH)
9.7
Excellent
·
Southold
·
2 br
·
Sleeps 4
·
Beach · Oven · In Unit Laundry ·
From
$425/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Wheelchair Accessible
Other spaces
Kitchen
Beautiful Waterfront Paradise In Southold - No Security Deposit
10
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
Waterfront · Fitness Center · Workspace ·
From
$663/nightProperty
House · 4 Beds · 4 baths
Amenities
Waterfront
Fitness Center
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Contemporary Colonial home with pristine Peconic bay views, steps to...
No reviews
·
Southold
·
5 br
·
Sleeps 10
·
High Ceilings · Walk In Closets · Balcony ·
From
$949/nightProperty
House · 5 Beds · 4 baths
Amenities
High Ceilings
Walk In Closets
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
9.9
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
Deck · Hot Tub · Balcony ·
From
$777/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Waterfront
Fitness Center
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Deck, Balcony, Kitchen
North Fork Has it ALL!
No reviews
·
Southold
·
3 br
·
Sleeps 6
·
Private Pool · Pool · Outdoor Space ·
From
$386/nightProperty
House · 3 Beds · 2 baths
Amenities
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach
9.6
Excellent
·
Southold
·
6 br
·
Sleeps 14
·
Balcony · Private Pool · Pool ·
From
$1,159/nightProperty
House · 6 Beds · 5 baths
Amenities
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Midcentury North Fork Beach House walking distance to beach
10
Excellent
·
Southold
·
3 br
·
Sleeps 6
·
High Ceilings · Workspace · Beach ·
From
$443/nightProperty
House · 3 Beds · 1 bath
Amenities
High Ceilings
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Waterfront, private beach, ready for adventure, flexcation!
10
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
Deck · Walk In Closets · Waterfront ·
From
$508/nightProperty
House · 4 Beds · 3 baths
Amenities
Walk In Closets
Waterfront
Fitness Center
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Deck, Workspace, Kitchen
Beautiful brand-new house steps from water!
No reviews
·
Southold
·
4 br
·
Sleeps 8
·
Waterfront · Beach · Outdoor Space ·
From
$573/nightProperty
House · 4 Beds · 4 baths
Amenities
Waterfront
Beach
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Cute Cottage Apartment Near town, beaches and vineyards (WBH)
9.6
Excellent
·
Southold
·
2 br
·
Sleeps 4
·
Beach · Outdoor Space · Oven ·
From
$430/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Wheelchair Accessible
Other spaces
Kitchen
House of Classic Arts and Crafts North Fork
9.6
Excellent
·
Southold
·
3 br
·
Outdoor Space · In Unit Laundry · Wifi ·
From
$283/nightProperty
House · 3 Beds · 2 baths
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
Spectacular waterfront property, with magnificent views from all sides.
10
Excellent
·
Southold
·
3 br
·
Sleeps 8
·
Deck · Balcony · Waterfront ·
From
$675/nightProperty
House · 3 Beds · 3 baths
Amenities
Waterfront
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Deck, Balcony, Kitchen
3BR Goose Creek Cottage: Southold,near beach & Greenport
No reviews
·
Southold
·
3 br
·
Sleeps 5
·
Balcony · Pool · Fitness Center ·
From
$526/nightProperty
House · 3 Beds · 2 baths
Amenities
Pool
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Balcony, Workspace, Kitchen
Gorgeous Estate with Pool by Beach, Lighthouse, Wineries & Farmers Market
10
Excellent
·
Southold
·
5 br
·
Sleeps 11
·
Carpet · Lake · Walk In Closets ·
From
$1,015/nightProperty
House · 5 Beds · 6 baths
Amenities
Carpet
Lake
Walk In Closets
Hot Tub
Private Pool
Waterfront
Pool
Beach
Other spaces
Kitchen
Lovely, Serene and Stylish Country Home
9.3
Excellent
·
Southold
·
3 br
·
Sleeps 4
·
Fitness Center · Outdoor Space · Oven ·
From
$362/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
North Fork Hideaway *14night MINIMUM
9.9
Excellent
·
Southold
·
4 br
·
Sleeps 8
·
Ocean · High Ceilings · Private Pool ·
From
$817/nightProperty
House · 4 Beds · 3 baths
Amenities
Ocean
High Ceilings
Private Pool
Waterfront
Pool
Beach
Oven
Dishwasher
Other spaces
Kitchen
Renovated American Farmhouse in the heart of Southold with heated saltwater pool
9.9
Excellent
·
Southold
·
4 br
·
Sleeps 8
·
Private Pool · Pool · Fitness Center ·
From
$654/nightProperty
House · 4 Beds · 2 baths
Amenities
Private Pool
Pool
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Workspace, Kitchen
Boutique Waterfront Home w/ Pool in Southold, LI
10
Excellent
·
Southold
·
4 br
·
Sleeps 12
·
Balcony · Workspace · In Unit Laundry ·
From
$325/nightProperty
House · 4 Beds · 3 baths
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Balcony, Workspace, Kitchen
Estate Living in the heart of Southold
No reviews
·
Southold
·
8 br
·
Sleeps 16
·
Ev Charging · Balcony · Private Pool ·
From
$1,134/nightProperty
House · 8 Beds · 7 baths
Amenities
Ev Charging
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Other spaces
Balcony, Workspace, Kitchen
Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards
9.5
Excellent
·
Southold
·
3 br
·
Sleeps 6
·
Balcony · Waterfront · Pool ·
From
$679/nightProperty
House · 3 Beds · 2 baths
Amenities
Waterfront
Pool
Fitness Center
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Waterfront Oasis on the North Fork
10
Excellent
·
Southold
·
4 br
·
Sleeps 8
·
Waterfront · Workspace · Beach ·
From
$450/nightProperty
House · 4 Beds · 2 baths
Amenities
Waterfront
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
NORTH FORK CHARM WITH 5 BEDROOM WITH WATER VIEWS AND WALK TO PRIVATE BEACH
10
Excellent
·
Southold
·
5 br
·
Sleeps 10
·
Oven · Dishwasher · In Unit Laundry ·
From
$620/nightProperty
House · 5 Beds · 3 baths
Amenities
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Southold Escape with Large Pool on Wine Trail
9.4
Excellent
·
Southold
·
3 br
·
Sleeps 6
·
Workspace · Beach · Air Conditioning ·
From
$448/nightProperty
House · 3 Beds · 3 baths
Amenities
Beach
Air Conditioning
Furnished
Swimming Pool
Residents Lounge
Other spaces
Workspace, Kitchen
Luxury by the Sea
10
Excellent
·
Southold
·
3 br
·
Sleeps 8
·
Fireplace · Dishwasher · In Unit Laundry ·
From
$498/nightProperty
House · 3 Beds · 3 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Storage
Other spaces
Kitchen
Charming Northfork home.
9.9
Excellent
·
Southold
·
3 br
·
Sleeps 6
·
Hardwood Floor · Beach · Outdoor Space ·
From
$399/nightProperty
House · 3 Beds · 2 baths
Amenities
Hardwood Floor
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Farmhouse Retreat
No reviews
·
Southold
·
1 br
·
Sleeps 4
·
Private Pool · Pool · Outdoor Space ·
From
$400/nightProperty
House · 1 Bed · 1 bath
Amenities
Private Pool
Pool
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Stargazing in North Fork - fireplace/pool/family friendly
No reviews
·
Southold
·
4 br
·
Sleeps 8
·
Furnished · Outdoor Space ·
From
$595/nightProperty
House · 4 Beds · 3 baths
Amenities
Furnished
Exquisite Private Retreat
No reviews
·
Southold
·
5 br
·
Sleeps 18
·
Hot Tub · Private Pool · Pool ·
From
$1,400/nightProperty
House · 5 Beds · 5 baths
Amenities
Hot Tub
Private Pool
Pool
Fitness Center
Beach
Fireplace
Oven
Dishwasher
Other spaces
Kitchen
Charming English Tudor
10
Excellent
·
Southold
·
4 br
·
Sleeps 10
·
On Site Laundry · Fireplace · Dishwasher ·
From
$1,500/nightProperty
House · 4 Beds · 3 baths
Amenities
On Site Laundry
Fireplace
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Fitness Center
Other spaces
Kitchen
Showing 1 - 50 of 88 results
Updated: March 22, 2023
Learn about vacation rentals in
Southold
Explore 88 vacation rentals near Southold, New York. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Southold, you can see photos of Southold vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Southold vacation rentals in specific areas. Whether you’re looking for a Southold staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Southold is $148 per night and the highest price is $1,500 per night.
77 of the vacation rentals near Southold are houses.
The average bathroom count for a vacation house near Southold is
3. The average price for vacation houses near Southold is $637 per night. There are 44 vacation homes under this price. The most common
amenities for vacation rentals near Southold are: furnished, outdoor space, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
2 available
2 bed rentals
16 available
3 bed rentals
27 available
4+ bed rentals
43 available
Getting around Southold
Walking
2/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Car
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
1/10
FYI, there are little to no public transit options within walking distance.
Points of interest in Southold
Groceries
2/10
No grocery stores within walking distance
Shopping
1/10
Few or no shops within walking distance
Cafes
1/10
Few or no cafés within walking distance
Restaurants
2/10
Few or no restaurants within walking distance
Nightlife
0/10
Few or no bars within walking distance
Vacation Rentals in Southold, NY FAQ
How many vacation rentals in Southold are available?
There are currently 88 vacation rentals in Southold available. Our vacation rentals in Southold include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Southold?
Yes, right now there are 35 pet friendly vacation rentals in Southold. A pet friendly vacation rental in Southold means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Southold with a pool?
Yes there are vacation rentals with a pool available in Southold, NY. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Southold with internet access?
As of March 22, 2023, there are vacation rentals with internet access available in Southold, New York. Check out more enjoyable destinations on Vacations by Zumper.
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