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Southold Vacation Rentals

Hotels (3)

B&Bs / Inns (7)

Specialty Lodging (1)

Vacation Rentals (46)

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O2C27, Old Lyme
O2C27
    Price: €604 - €838/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O3CO55, Old Lyme
O3CO55
    Price: €764 - €1,059/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O2C65, Old Lyme
O2C65
    Price: €681 - €859/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 1
    • Contact Manager
O2W54, Old Lyme
O2W54
    Price: €769 - €1,066/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 1
    • Contact Manager
O3C28, Old Lyme
O3C28
    Price: €1,088 - €1,381/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 1
    • Contact Manager
O2P35, Old Lyme
O2P35
    Price: €802 - €1,059/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O1W55, Old Lyme
O1W55
    Price: €1,237 - €1,558/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 1
    • Contact Manager
O6B57, Old Lyme
O6B57
    Price: €1,127 - €1,412/week
  • Bedrooms: 3, sleeps 7
  • Bathrooms: 2
    • Contact Manager
O4S46U, Old Lyme
O4S46U
    Price: €609 - €831/week
  • Bedrooms: 4, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O1W62, Old Lyme
O1W62
    Price: €1,246 - €1,973/week
  • Bedrooms: 4, sleeps 7
  • Bathrooms: 2
    • Contact Manager

Search Southold Vacation Rentals


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Vacation rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]

There are no vacation rentals within Southold, North Fork, Long Island, New York. We broadened your search to include all rentals within 25 miles.

O1N19, Old Lyme
O1N19
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 1
For the economy minded, this cottage is one of the best bargainsat the beach. Recreation program for kids, near all the necessities including a new community ...
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PURPLE BUTTON FACTORY, Guilford
PURPLE BUTTON FACTORY
Contact Owner
Nightly rate from
€173
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 9
Bathrooms: 2
Min stay:7
THE PURPLE BUTTON FACTORY. Charming, totally remodeled, close to center of town, restaurants, shopping and 5 min to the beaches. 2,000 sq ft Sleeps 8 in ...
  • Nightly
    €173
  • Weekly
    €1,177
  • Monthly
    €3,462
SPECTACULAR OCEANFRONT HAMPTONS BEACH HOME-DUNE RD, Westhampton
SPECTACULAR OCEANFRONT HAMPTONS BEACH HOME-DUNE RD
Contact Owner
Nightly rate from
€692
Management: Verified owner
Property: Rental Home
Bedrooms: 8, sleeps 16
Bathrooms: 8
Min stay:1
8 bedrooms, 8 baths (6 full, 2 half); sleeps 16. Rock-star type oceanfront house in West Hampton Dunes, LI. 2007 construction, 5000 square feet, on nearly 90 ...
  • Nightly
    €692
  • Weekly
    €4,847
  • Monthly
    €17,311
Charming Beach House with Spectacular Views, Westbrook
Charming Beach House with Spectacular Views
Contact Owner
Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Gorgeous September weeks available. This 4 bedroom 1920's beach house has been totaly renovated within the year. Hardwood floors throughout, a brand new ...
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  • Weekly
    €1,212 - €1,368
  • Monthly
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Caribbean Style Cottage Across from Water & Beach, Shelter Island
Caribbean Style Cottage Across from Water & Beach
Contact Owner
Nightly rate from
€225
Management: Verified owner
Property: Rental Home
Bedrooms: 2, sleeps 4
Bathrooms: 2
Long Island NY Zen-Like Caribbean Euro Style Secluded Cottage Rental across from Beach and waterfront in Estate section of Shelter Island. A weeks stay at ...
  • Nightly
    €225
  • Weekly
    €1,385 - €2,493
  • Monthly
    €5,089 - €7,617
O1N49, Old Lyme
O1N49
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Only five houses from sandy beach. Constant favorable comments.Comfortable older remodeled home with modern natural flare.15 miles from New London, USCG, ...
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  • Weekly
    €1,061 - €1,470
  • Monthly
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O1N09, Old Lyme
O1N09
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
Comfortable family cottage 3 min walk to sandy beach.Treed yard for cook outs etc. Policy: Smoking not allowed, Pets not allowed Minimum Stay: 1 ...
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O3CO36, Old Lyme
O3CO36
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
Luxurious vacationing at the beach. Pristine three bedroom two bath home in the Miami Beach gated community.Large deck off comfortable sunroom. Tastefully ...
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  • Weekly
    €1,327 - €1,752
  • Monthly
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O6SL15, Old Lyme
O6SL15
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 9
Bathrooms: 2
Delightful direct waterfront panoramic views of Long Island Sound and sandybeach. Grand living rm w/ fireplace and screened front porch face the beach. Enjoy ...
  • Nightly
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  • Weekly
    €1,813 - €2,514
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O2W42, Old Lyme
O2W42
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 1
Excellent condition cottage. Enjoy lounging with sand in your toes! ...or yep! its now time for a dip in Long Island Sound. Swim your own lovely beach at ...
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  • Weekly
    €1,345 - €1,775
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O3B46, Old Lyme
O3B46
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 1
Economy minded, all basics, comfortable and near the beach - 4 minute walk. Shopping, recreation facilities all nearby. Policy: Smoking not allowed, Pets not ...
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  • Weekly
    €635 - €838
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O3F31, Old Lyme
O3F31
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
A very nice cottage well equipped within eazy walk of private sandy beach. Beach side parking provided for residents of this private gated community. Policy: ...
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  • Weekly
    €604 - €838
  • Monthly
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O6S53, Old Lyme
O6S53
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
A nice year round beach home w/ water view. Many conveniences, Large mowed yard.Near stores, galleries, boating, deep sea fishing ,casinos, private ...
  • Nightly
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  • Weekly
    €1,000 - €1,386
  • Monthly
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O1S44, Old Lyme
O1S44
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
Delightful ocean view ranch style cottage close beach on private roadway.Lots of parking, marsh views, open decks for outdoor living. Truly a year round four ...
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  • Weekly
    €830 - €1,150
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O5O824, Old Lyme
O5O824
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 5
Bathrooms: 1
Wonderful sandy beach front, panoramic views sun rise to sun set of LI Sound from deck.Parking 1 car at unit, 1 at private lot, 1 block away. Policy: Pets not ...
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  • Weekly
    €906 - €1,257
  • Monthly
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Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns