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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 43 Villas in Southold with updated reviews, rates, and availability.

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
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, (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
Villa Flasses
Pool

Villa Flasses

3.0 star property
Villa Flasses
Villa Direen Modern East Hampton Villa
Exterior

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
Villa Spectrum
Porch

Villa Spectrum

3.5 star property
Villa Spectrum
Villa Edwards Hole
Outdoor pool

Villa Edwards Hole

3.0 star property
Villa Edwards Hole
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
Villa Keylime
Front view of the property

Villa Keylime

2.0 star property
Villa Keylime
Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton
Pool

Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton

2.0 star property
Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton
Villa Coastal Bliss
Bathroom

Villa Coastal Bliss

Villa Coastal Bliss
Villa Gally
Outdoor pool

Villa Gally

2.0 star property
Villa Gally
YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Exterior

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Villa Emery
Front view of the property Outdoor pool

Villa Emery

2.0 star property
Villa Emery
Chic Modern Retreat In Wainscott
Exterior

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
Pool view Garden Property Building Swimming Pool Sun lounger

Experience Serene Luxury: Villa Direen, Your East Hampton Escape

2.0 star property
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
Pool

Discover Luxury and Serenity at Villa Edwards Hole in East Hampton

2.0 star property
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
Villa Vajra
Pool

Villa Vajra

2.0 star property
Villa Vajra
Villa Lavender
Pool

Villa Lavender

3.5 star property
Villa Lavender
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, (273)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is SAR 494
SAR 645 total
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort
Stunning Hampton Holiday Family Fantasy for your Team
Safety gates, privet-enclosed, private pool, spa, and pool house.

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team
10 Bedroom Hampton House with a regulation size Pickleball
Pool

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
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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