Compare Southold Villas

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Featured Villas in Southold

Hampton Private Retreat - last minute offer June 23-

Hampton Private Retreat - last minute offer June 23-

Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.
Pool
Kitchen
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

$1,406 nightly
The price is $1,606 total per night
$1,606 total
Aug 4 - Aug 5
Total includes taxes and fees
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
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

Guests staying at this villa enjoy a hot tub, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
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 garden, and a picnic area. You can take advantage of free parking, along with an airport shuttle (available on request) for USD 200 per vehicle. This villa also has barbecue grills.
Pool
Washer
Villa Flasses

Villa Flasses

3 out of 5
94 Spring Pond Ln, Southampton, NY
Guests staying at this villa can enjoy an outdoor pool, a garden, and barbecue grills. 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 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 picnic area, and a garden.
Pool
Kitchen
Fabulous familly villa in East hampton village fringe

Fabulous familly villa in East hampton village fringe

At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Villa Verde - Sanctuary @ Bridge

Villa Verde - Sanctuary @ Bridge

Guests of this villa have access to an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and a garden.
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
    $397 nightly
    The price is $450 total per night from Aug 13 to Aug 14
    $450 total
    Aug 13 - Aug 14
    Total includes taxes and fees
    9.4/10 Exceptional! (186 reviews)
    Vine & Sand

    Vine & Sand

    47100 New York 25, Southold, NY
    10/10 Exceptional! (8 reviews)
    Quality Inn Old Saybrook - Westbrook

    Quality Inn Old Saybrook - Westbrook

    100 Essex Rd, Old Saybrook, CT
    $111 nightly
    The price is $127 total per night from Aug 6 to Aug 7
    $127 total
    Aug 6 - Aug 7
    Total includes taxes and fees
    7.6/10 Good! (1,015 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
38 Villas
Lowest Price
$127
Highest Price
$1,606
Popular accommodation
Hampton Private Retreat - last minute offer June 23-, 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, Villa Direen Modern East Hampton Villa, Villa Flasses, Villa Isaiah, Fabulous familly villa in East hampton village fringe, Villa Verde - Sanctuary @ Bridge

Villas in Southold

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