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Compare 45 Villas in Southold with updated reviews, rates, and availability.

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Pool
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
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Exterior
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
10.0 out of 10, Exceptional, (15)
"It was perfect "
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
New Construction Greenport Pool House - 3 Blocks from Town
Pool
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
Villa Direen Modern East Hampton Villa
Exterior
Villa Direen Modern East Hampton Villa
3.5 star property
Villa Direen Modern East Hampton Villa
Villa Flasses
Pool
Villa Flasses
3.0 star property
Villa Flasses
Iconic Charles Moore Springs home with dock and our home is pet-friendly
Miscellaneous
Iconic Charles Moore Springs home with dock and our home is pet-friendly
2.0 star property
10.0 out of 10, Exceptional, (1)
"My family really enjoyed staying at this special property, and the direct access to the water was icing on the cake! Britta was a fantastic, responsive host."
Iconic Charles Moore Springs home with dock and our home is pet-friendly
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
Exterior
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
Luxurious beach house on the Long Island sound
Living area
Luxurious beach house on the Long Island sound
Luxurious beach house on the Long Island sound
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Property grounds
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
Chic Modern Retreat In Wainscott
Exterior
Chic Modern Retreat In Wainscott
Chic Modern Retreat In Wainscott
Villa Lavender
Pool
Villa Lavender
3.5 star property
Villa Lavender
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Exterior
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Villa Nostro Palazzo
Terrace/patio
Villa Nostro Palazzo
4.0 star property
Villa Nostro Palazzo
Villa Vajra
Exterior
Villa Vajra
3.5 star property
Villa Vajra
Villa Sofia
Outdoor pool
Villa Sofia
3.5 star property
Villa Sofia
Villa Isaiah
Front of property
Villa Isaiah
3.5 star property
Villa Isaiah
Beautiful villa
Pool
Beautiful villa
Beautiful villa
Villa Skylar
Front of property
Villa Skylar
3.5 star property
Villa Skylar
Villa Spectrum
Porch
Villa Spectrum
3.5 star property
The price is SAR 7,884
SAR 11,727 total
includes taxes & fees
23 Nov - 24 Nov
Villa Spectrum
Fabulous familly villa in East hampton village fringe
Interior
Fabulous familly villa in East hampton village fringe
Fabulous familly villa in East hampton village fringe
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
Property grounds
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is SAR 474
SAR 623 total
includes taxes & fees
3 Dec - 4 Dec
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Room
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Heated 40ft saline pool and deck in separate secure fenced area with all day sun
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (166)
"Perfect family home"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
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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