Compare Southold Villas

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Featured Villas in Southold

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

Guests staying at this villa can enjoy an outdoor pool, barbecue grills, and a garden.
Pool
Kitchen
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Guests staying at this villa enjoy an outdoor pool, a hot tub, and barbecue grills. This smoke-free villa also has a garden.
Pool
Hot Tub
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

This villa features a hot tub and a garden. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Hampton Private Retreat - last minute offer June 23-

Hampton Private Retreat - last minute offer June 23-

Guests staying at this villa enjoy a gym, a hot tub, and barbecue grills. This smoke-free villa also has a garden.
Pool
Hot Tub
Villa Flasses

Villa Flasses

3 out of 5
94 Spring Pond Ln, Southampton, NY
Guests staying at this villa can enjoy an outdoor pool, barbecue grills, and a garden. There's free parking, and an airport shuttle (available on request) for USD 200 per vehicle. This villa also has a picnic area.
Pool
Parking included
Villa Direen Modern East Hampton Villa

Villa Direen Modern East Hampton Villa

3.5 out of 5
137 Stephen Hands Path, East Hampton, NY
Guests staying at this villa can enjoy an outdoor pool, a picnic area, and barbecue grills. You can take advantage of free parking, along with an airport shuttle (available on request) for USD 200 per vehicle. This villa also has a garden.
Pool
Washer
Live on the Water: Dock, Beach, Boat, Kayak & Fish

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

Guests staying at this villa enjoy a gym, a hot tub, and a garden. This family-friendly villa also has barbecue grills.
Hot Tub
Kitchen
Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound

Guests staying at this villa enjoy features like a gym.
Washer
Dryer
Villa Isaiah

Villa Isaiah

3.5 out of 5
286 Montauk Highway, Southampton, NY
Guests of this villa enjoy features like an outdoor pool, free WiFi in public areas, and free newspapers. Free valet and self parking are available—or if you're not driving, take the airport shuttle (available on request) for USD 200 per vehicle. Staff members are on hand to provide dry cleaning/laundry services, concierge services, and luggage storage. Additional amenities include laundry facilities, a garden, and a picnic area.
Pool
Kitchen
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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.

Hotel Options in Southold

    The Shoals Suites and Slips

    The Shoals Suites and Slips

    61600 Main Rd, Southold, NY
    The price is $240 per night from Apr 6 to Apr 7
    $240
    includes taxes & fees
    $213 per night
    Apr 6 - Apr 7
    9.4/10 Exceptional! (155 reviews)
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road, Westbrook, CT
    The price is $246 per night from Apr 6 to Apr 7
    $246
    includes taxes & fees
    $214 per night
    Apr 6 - Apr 7
    8.6/10 Excellent! (1,000 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd, Old Saybrook, CT
    The price is $91 per night from Apr 6 to Apr 7
    $91
    includes taxes & fees
    $79 per night
    Apr 6 - Apr 7
    7.6/10 Good! (936 reviews)

Luxury Villas

Book luxury villas in Southold
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Southold. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Southold, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Southold
You won’t have a problem finding your own space in Southold. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Southold on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Southold rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Southold Villas essential information

Accommodation
51 Villas
Lowest Price
$91
Highest Price
$246
Popular accommodation
1.5 Acre Luxury Escape - Saltwater Pool with Water Views, New Construction Greenport Pool House - 3 Blocks from Town, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Hampton Private Retreat - last minute offer June 23-, Villa Flasses, Villa Direen Modern East Hampton Villa, Live on the Water: Dock, Beach, Boat, Kayak & Fish, Luxurious beach house on the Long Island sound, Villa Isaiah

Villas in Southold

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