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Check prices for these dates

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Aug 15 - Aug 17
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Browse Select Southold Condo Rentals

Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Relax on a serene coastal deck with a view of the calm sea.

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

10.0 out of 10, Exceptional, (76)
"Property was amazing "
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Shelter Island Waterview Villa
Relax in a serene outdoor space surrounded by lush greenery and framed by large windows.

Shelter Island Waterview Villa

Shelter Island Waterview Villa
Elegant Hamptons Hideaway w/ Path to Beach!
Relax in a warm, inviting space with a large bed, functional workspace, and kitchen area.

Elegant Hamptons Hideaway w/ Path to Beach!

6.0 out of 10, (1)
"The property is very well located near the beach and has a nice outdoor area. It's important to know that the three spaces are separate, and the only full bathroom is on the upper floor with external stairs to reach it. Certain things were broken around the property (screen door on the 2nd floor was ripped, not all blinds functioned fully), things that should not be present at this price point."
Elegant Hamptons Hideaway w/ Path to Beach!
nice condo
Enjoy meals in the kitchen with a central island, oven, and stainless steel sink.

nice condo

nice condo
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Experience the hotel's elegant design, featuring a spacious pool area with lounge chairs and balconies on each floor.

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.
Relax in a serene outdoor space surrounded by lush greenery and a brick wall, featuring a sofa and small table.

Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.

Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.
Happy Days in Hampton Bays
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, ample counter space, and pendant lighting.

Happy Days in Hampton Bays

Happy Days in Hampton Bays
Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Enjoy a serene beachside view from this balcony, overlooking a sandy shore and calm sea.

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Beautiful Waterfront Condo
Relax in this stylish living room with a large flat-screen TV, comfortable seating area, and a cozy coffee table.

Beautiful Waterfront Condo

Beautiful Waterfront Condo
Southampton condo close to beach and village
Enjoy al fresco dining or relaxation in this serene outdoor space with a table and chairs, surrounded by lush greenery and a garden fence.

Southampton condo close to beach and village

Southampton condo close to beach and village
Million Dollar Sunsets Overlooking Bayfront Beach
Relax by the pool surrounded by comfortable lounge chairs and shaded areas.

Million Dollar Sunsets Overlooking Bayfront Beach

Million Dollar Sunsets Overlooking Bayfront Beach
Pools tennis gym golf pickelball
Relax by the pool surrounded by lush greenery and enjoy a refreshing swim in the clear waters.

Pools tennis gym golf pickelball

Pools tennis gym golf pickelball
Beautiful Beach Front 1 Bedroom Triplex
Stroll through the beautifully maintained garden pathway to the central lawn area, surrounded by neatly trimmed hedges and shrubs.

Beautiful Beach Front 1 Bedroom Triplex

Beautiful Beach Front 1 Bedroom Triplex
Southampton Village Condo
Relax by the serene pool surrounded by lush greenery and trees, with lounge chairs and umbrellas providing shade.

Southampton Village Condo

Southampton Village Condo
Amagansett Beachfront Beauty
House, Multiple Beds (Amagansett Beachfront Beauty)

Amagansett Beachfront Beauty

4.0 star property
Amagansett Beachfront Beauty
Heaven in the Hamptons
Relax on the patio with comfortable seating and shade from two umbrellas, overlooking a serene pool and lush surroundings.

Heaven in the Hamptons

Heaven in the Hamptons
Mattituck Marvel
House, Multiple Beds (Mattituck Marvel) | Exterior

Mattituck Marvel

4.0 star property
Mattituck Marvel
Cozy 2-bedroom condo with AC, fitness room in charming Westbrook. Oceanfront,
Living area

Cozy 2-bedroom condo with AC, fitness room in charming Westbrook. Oceanfront,

Cozy 2-bedroom condo with AC, fitness room in charming Westbrook. Oceanfront,
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Friendly staff, good restaurant "
Barbara 5-night trip
Posted 2 days ago
Saybrook Point Resort & Marina