Southold Vacation Rentals
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5 km
110 rentals in Southold.
Newly Renovated Gem on the Cedar Beach Peninsula!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southold near vineyard & beach
Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 7
Match: Sleeps
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Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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5BR Beach House, In Ground Heated Salt Water Pool, Walk to Private Beach!
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Room 2--King Bed and Ensuite Bathroom With Rain Shower
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vine + Sand--Southold, NY'S Newest B&B Room 1--King Bed and Ensuite Bathroom
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Cottage on North Fork
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Farmhouse Retreat
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Southold Soundfront Private Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Entire Loft-Walk to Town, Beach, Train, Wine Trail
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Southold Cottage w/ Patio & Grill - Walk to Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cute Cottage Apartment Near town, beaches and vineyards (WBH)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Fork Retreat
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming house walking distance from beautiful Kenney’s Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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LI Sound view, walk to beaches,lake access/kayaking, fishing
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Classic North Fork Beach Home
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Southold by the bay
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Seaside Southold Escape in Private Beach Community
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Waterview Cottage in the Heart of Long Island Wine country
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful private home with beach access down the block
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Fork Waterfront Spectacular Views Cottage circa 1930
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful waterfront house in Southold
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cottage on private road and 5-min walk to beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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House central to North Fork wineries restaurants + beaches. Walk to town.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Midcentury North Fork Beach House walking distance to beach
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy Wine Country and Walk The Beautiful Beach At Sunset
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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House of Classic Arts and Crafts North Fork
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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3 Bedroom NoFo Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Northfork home.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Beach House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to train and town
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage by Cedar Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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North Fork Waterfront Gem!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming, Historic Farmhouse close to restaurants, vineyards and beach.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunny and quiet home - steps from the bay!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NorthFork Serenity, next to beach and wineries
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely, Serene and Stylish Country Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 110
Frequently Asked Questions about Southold
- Yes, here are some popular vacation rentals in Southold that have a pool:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
- Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Yes, here are some popular vacation rentals in Southold that have internet access:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
- Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
- The best pet friendly rentals in Southold are:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
- Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
- Some of the most popular kid friendly rentals in Southold are:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
- Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
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