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Compare 51 Villas in Southold with updated reviews, rates, and availability.

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
10.0 out of 10, Exceptional, (1)

New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
10.0 out of 10, Exceptional, (17)

Hampton Private Retreat - last minute offer June 23-
Hampton Private Retreat - last minute offer June 23-
10.0 out of 10, Exceptional, (19)

Villa Flasses
Villa Flasses

Villa Direen Modern East Hampton Villa
Villa Direen Modern East Hampton Villa

Live on the Water: Dock, Beach, Boat, Kayak & Fish
Live on the Water: Dock, Beach, Boat, Kayak & Fish
10.0 out of 10, Exceptional, (1)

Luxurious beach house on the Long Island sound
Luxurious beach house on the Long Island sound
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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Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape
North Fork 7 Bedroom Farmhouse Escape
9.4 out of 10, Exceptional, (3)

Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (284)
The price is AED 565
AED 725 total
includes taxes & fees
18 May - 19 May

Cliffside Resort Condominiums
Cliffside Resort Condominiums
9.0 out of 10, Wonderful, (215)
The price is AED 854
AED 1,135 total
includes taxes & fees
26 May - 27 May
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.
Recent reviews of Southold hotels
Recent reviews of Southold hotels

Water's Edge Resort & Spa
5/5 Excellent
"My boyfriend and I came here for the first time for a little getaway for his birthday and we had such a lovely time. Everything was perfect! Spa, the private beach area & Datillo’s restaurant is top tier. Thank you Water Edge for a fantastic stay! We will be back again!"
A verified traveler stayed at Water's Edge Resort & Spa
Posted 1 day ago
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