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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

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

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

10.0 out of 10, Exceptional, (17)
"This is a large and extremely comfortable house. The owner is attentive to any questions you might have. LOVED spending time there. "
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"We enjoyed Connie’s beautiful home. The kitchen was fully stocked, the bedrooms were very comfortable and the location was perfect. My family would definitely stay here again!"
Hampton Private Retreat - last minute offer June 23-

Villa Flasses

3.0 star property
Villa Flasses

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa

Live on the Water: Dock, Beach, Boat, Kayak & Fish

10.0 out of 10, Exceptional, (1)
"I have rented many houses in the Hamptons and this was the best by far! Family friendly, great hosts and magical spot!"
Live on the Water: Dock, Beach, Boat, Kayak & Fish

Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound

Villa Isaiah

3.5 star property
Villa Isaiah

Villa Spectrum

3.5 star property
Villa Spectrum

Villa Skylar

3.5 star property
Villa Skylar

Villa Vajra

3.5 star property
Villa Vajra

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott

Villa Nostro Palazzo

4.0 star property
Villa Nostro Palazzo

Beautiful villa

Beautiful villa

TBD by Rove Travel 7BR Pool Hot Tub

2.0 star property
TBD by Rove Travel 7BR Pool Hot Tub
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

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 605
AED 771 total
includes taxes & fees
12 May - 13 May
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (210)
"Very beautiful location and the room unforgettable ocean view will definitely come back"
The price is AED 638
AED 889 total
includes taxes & fees
7 May - 8 May
Cliffside Resort Condominiums

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!
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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