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Vacation Rentals in Southold

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Spectacular Waterfront home on Southold bay - one of a kind! – Property 281433

  • Southold rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, balcony
  • $1,000 - $3,500/week
  • Calendar Last Updated On: Mar 18, 2010
Located in the private beach community of Reydon Shores, 'The Roost' was newly built in 2007-2008. This property is bordered by over 400 acres of forever wild...

Direct waterfront home with private sandy beach and floating dock – Property 270838

  • Southold rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, garden
  • $1,200 - $5,000/week
  • Calendar Last Updated On: Mar 18, 2010
Our non-smoking, waterfront beach house is beautifully appointed on almost two acres of private and completely natural preserve, at the heart of Long Island's North...

Lakefront Cottage, Walk to Beach, Hot Tub, Beautiful Sunsets – Property 115439

  • Southold rental - house, 2 bedrooms, sleeps 4, beach, waterfront, garden
  • $1,000 - $1,700/week
  • Calendar Last Updated On: Mar 17, 2010
This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town...

North Fork Waterfront, Pool, Golf, Celebration,Spring Vac, 5 star living! – Property 253123

  • Southold rental - house, 5 bedrooms, sleeps 12, 5 bathrooms, 1 half bath, resort, waterfront, daily maid service
  • $2,500 - $9,000/week
  • Calendar Last Updated On: Mar 16, 2010
Perfect for people or families who want a vacation property with style, elegance and extraordinary amenities. The heated gunite pool and all decks have cable fencing...

Deeded Bay Beach Home – Property 184107

  • Southold rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, rural, air-conditioning
  • $1,400 - $2,000/week
  • Calendar Last Updated On: Mar 16, 2010
This beautiful home is located in a private and quiet beach community in Southold, New York. It's the perfect place to relax and take in the North Fork's pristine...

The Waterfront Loft in Southold – Property 281432

  • Southold rental - cottage, 1 bedroom, sleeps 4, 1 bathroom, beach, waterfront, air-conditioning
  • $850 - $1,250/week
  • Calendar Last Updated On: Mar 18, 2010
Breathtaking Waterfront Loft on Southold Bay with efficiency kitchenette; fridge/microwave/coffeemaker. * Queen size Bed with the best pillow top mattress available...

Charming Waterfront Home with Private Dock Close to Vineyards & Beaches – Property 237018

  • Southold rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, terrace
  • $1,200 - $1,690/week
  • Calendar Last Updated On: Mar 10, 2010
Wonderful year round home with 3 bedrooms and 2 Bathrooms. Private Dock accommodates boat up to 22 feet. Floating dock is great for launching your kayak or canoe.

North Fork private summer paradise close to all – Property 238054

  • Southold rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, village, garden
  • $1,300 - $2,200/week
  • Calendar Last Updated On: Mar 10, 2010
Stay in our beautiful Southold home around the corner from LI Sound beach McCabe's Beach. Sit out on your spacious screened porch and enjoy the peace and privacy and...

2 Bedroom Apartment in Historic Home with private yard (WBH) – Property 185644

  • Southold rental - apartment, 2 bedrooms, sleeps 4, 1 bathroom, beach, village, garden
  • $750 - $875/week
  • Calendar Last Updated On: Mar 3, 2010
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own...

Water View Beach House with central AC located in Wine Country – Property 111053

  • Southold rental - house, 3 bedrooms, sleeps 7, 2 bathrooms, beach, resort, garden
  • $1,600/week
  • Calendar Last Updated On: Mar 1, 2010
Immaculate home in a private beach community. Completely renovated. Central A/C, hardwood and tile floors, deep soaking tub, duel fireplace and upgraded kitchen.

Cute Cottage Apartment Near town, beaches and vineyards (WBH) – Property 174265

  • Southold rental - cottage, 2 bedrooms, sleeps 4, 1 bathroom, beach, village, pets considered
  • $750 - $875/week
  • Calendar Last Updated On: Feb 22, 2010
Come listen to the bands while tasting the local wines (See local vineyards and events) , Walk to Southold Village or Beautiful Bay Beaches or just relax on your...

Historic vineyard farmhouse with fabulous sandy bay beach – Property 235741

  • Southold rental - farmhouse, 4 bedrooms, sleeps 8, 1 bathroom, 2 half baths, beach, rural, garden
  • $1,800 - $3,750/week
  • Calendar Last Updated On: Feb 7, 2010
Charming turn of the century farmhouse with forever vineyard views only a short 400ft stroll through the vines to your sugar sand beach on the Peconic Bay with views...

Lakefront Cottage with Deck, Walk to Beach – Property 122096

  • Southold rental - cottage, 2 bedrooms, sleeps 4, 1 bathroom, lake, waterfront, garden
  • $1,015 - $1,365/week
  • Calendar Last Updated On: Jan 24, 2010
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties...

Laid-Back Luxury - 1 Block to Beach - Private, Peaceful Oasis! – Property 273380

  • Southold rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, near the ocean, garden
  • Calendar Last Updated On: Jan 17, 2010
Stunning, spacious, light-filled, newly renovated contemporary with breathtaking water/nature preserve views from every room.

Lakefront House in Natural Setting, Walk to Beach – Property 135006

  • Southold rental - house, 2 bedrooms, sleeps 4, 1 bathroom, beach, lake, garden
  • $1,200 - $1,750/week
  • Calendar Last Updated On: Aug 22, 2009
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach.

Long Island's North Fork, Beautiful House, Private Beach, Woods – Property 164224

  • Southold rental - house, 4 bedrooms, sleeps 8, beach
  • Calendar Last Updated On: May 21, 2009
Enjoy a great family vacation on Long Island's North Fork. This 4 bedroom, 2 bath house is steps from a private bay front beach.
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