Southold Vacation Rentals
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132 rentals in Southold.
Newly Renovated Gem on the Cedar Beach Peninsula!
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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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Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite
Rental Home
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
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Farmhouse Retreat
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Entire Loft-Walk to Town, Beach, Train, Wine Trail
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Cute Cottage Apartment Near town, beaches and vineyards (WBH)
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North Fork Retreat
Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Classic North Fork Beach Home
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Cottage
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Seaside Southold Escape in Private Beach Community
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Cottage in the Heart of Long Island Wine country
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North Fork Waterfront Spectacular Views Cottage circa 1930
Rental Home
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Cottage on private road and 5-min walk to beach
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Amazing Beach House in the North Fork Wineries
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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House of Classic Arts and Crafts North Fork
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North Fork Beach House
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North Fork Waterfront Gem!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lovely home w/ water views, steps to beach!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kenneys Beach retreat by the Wineries
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
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Sea Breeze Paradise: Beachfront & Panoramic Views
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Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
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Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
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Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit
Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
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Cozy Long Island Escape
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NF Wine Country Retreat with Dock
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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90 feet of private waterfront w beach, new renovation, panoramic views
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury by the Sea
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Charming English Tudor
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Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beach Front in Southold; newly renovated/baths/kitchen/2nd floor family room!
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Beautifully appointed waterfront property with heated pool and cabana
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Stunning Home & Private Beach on the North Fork
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Unique Southold waterfront luxury home with heated pool on Long Creek
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Sprawling waterfront home with bikes, kayaks, pool table, and grill - dogs ok
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Panoramic Water Views, hot tub, fire pit & easy access to North Fork wine trail
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HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
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New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
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Beautiful waterfront house in Southold
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Hamptons Style/North Fork Chill and Grill. 1 mile to beaches. Onsite manager.
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LI Sound view, walk to beaches,lake access/kayaking, fishing
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Southold retreat-- Indoor/outdoor living near immaculate beaches
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southold Escape with Large Saltwater Pool on Wine Trail
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
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Contemporary Colonial home with pristine Peconic bay views, steps to...
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Waterfront Southold Retreat < 3 Mi to Wineries!
Rental Home
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 132
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!
- Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
- Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom
- Yes, here are some popular vacation rentals in Southold that have internet access:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
- Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom
- Some of the most popular kid friendly rentals in Southold are:
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
- Farmhouse Retreat
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