Owner Direct Beach Rentals in Southold

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277 Southold Beach Rentals From $208

Ready for a sun-soaked trip to Southold? Explore our index of beach house rentals and sunny coastal apartments. Owner Direct helps you filter through verified seaside options to find your next relaxing shore retreat.

Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
1.8k from Southold center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$391
Average price / night
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Charming Cottage
Charming Cottage
Cottage
Southold, NY, 11971, United States
0.5k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

37 reviews

$541
Average price / night
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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
1.8k from Southold center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$499
Average price / night
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Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
House
Southold, NY, 11971, United States
0.6k from Southold center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms9 Guests
9.8

Exceptional

6 reviews

$1092
Average price / night
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Minnehaha Marvel
Minnehaha Marvel
House
Southold, NY, USA
2.5k from Southold center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$296
Average price / night
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House of Classic Arts and Crafts North Fork
House of Classic Arts and Crafts North Fork
House
Southold, NY, 11971, United States
0.6k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$588
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
3.3k from Southold center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

3 Bedrooms6 Guests
New to Booking
$811
Average price / night
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Cozy studio with WiFi and AC in welcoming Southold
Cozy studio with WiFi and AC in welcoming Southold
Apartment
Southold, NY, 11971, United States
0.7k from Southold center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, Patio

1 Bedroom3 Guests
9.2

Superb

7 reviews

$333
Average price / night
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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
5.4k from Southold center

Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
Average price / night
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Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
House
Southold, NY, 11971, United States
0.9k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$399
Average price / night
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Walk to Beach Long Island Wine Country Home!
Walk to Beach Long Island Wine Country Home!
House
Cutchogue, NY, USA
6.3k from Southold center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Beach

3 Bedrooms7 Guests
New to Booking
$271
Average price / night
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Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
House
Southold, NY, 11971, United States
1.0k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$529
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
7.7k from Southold center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Founders Landing, Salt Water Heated Pool, Walk To Beach, Town, Restaurants
Founders Landing, Salt Water Heated Pool, Walk To Beach, Town, Restaurants
House
Southold, NY, 11971, United States
1.0k from Southold center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms6 Guests
New to Booking
$1422
Average price / night
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Lavender Bay Breezes - Private Bay Beach Community
Lavender Bay Breezes - Private Bay Beach Community
House
Southold, New York, USA
9.3k from Southold center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay, Accessible hotels

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
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Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
House
Southold, NY, 11971, United States
1.1k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
7.0

Good

2 reviews

$208
Average price / night
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Stylish beach getaway: pool in prime location
Stylish beach getaway: pool in prime location
House
Southold, NY, 11971, United States
1.2k from Southold center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$1078
Average price / night
Check Availability
Southold 3BR Waterfront Home on Goose Creek | Dock, Kayaks, Single-Level
Southold 3BR Waterfront Home on Goose Creek | Dock, Kayaks, Single-Level
House
Southold, NY, 11971, United States
1.2k from Southold center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

21 reviews

$820
Average price / night
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Charming Northfork home.
Charming Northfork home.
House
Southold, NY, 11971, United States
1.3k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$577
Average price / night
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NorthFork Serenity, next to beach and wineries
NorthFork Serenity, next to beach and wineries
House
Southold, NY, 11971, United States
1.3k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$666
Average price / night
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool
Renovated American Farmhouse in the heart of Southold with heated saltwater pool
House
Southold, NY, 11971, United States
1.3k from Southold center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$1263
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Beach Rentals in Southold.

Stay Near Southold's Top Attractions

OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Southold. If you plan on staying in the Southold area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Rentals in Southold

You can explore 277 verified beach rentals in Southold. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Southold vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $208 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Southold offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Southold welcome pets. Currently, 34 listings allow pets, although policies may vary by property. It's also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it's recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Southold often include amenities designed for coastal living, such as View, Ocean View, and Fireplace/Heating. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It's best to review the amenities section of each listing to confirm what is included and plan accordingly.