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-

Southampton NY
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
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Greenport NY
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

Hampton Bays NY
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
Iconic Charles Moore Springs home with dock and our home is pet-friendly

Iconic Charles Moore Springs home with dock and our home is pet-friendly

2 out of 5
East Hampton NY
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Washer
Dryer
Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA

Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA

Southampton NY
At this villa, guests enjoy an outdoor pool, a gym, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and 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
TBD by Rove Travel 7BR Pool Hot Tub

TBD by Rove Travel 7BR Pool Hot Tub

2 out of 5
Amagansett NY
TBD by Rove Travel 7BR Pool Hot Tub features free WiFi in public areas and a garden.
Free WiFi
Outdoor Space
Villa Sofia

Villa Sofia

3.5 out of 5
133 Stephen Hands Path East Hampton NY
At this villa, guests have access to an outdoor pool, a terrace, and barbecue grills. There's free parking, and an airport shuttle (available on request) for USD 200 per vehicle. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free villa also has 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
    $172 nightly
    The price is $197 total per night from Jan 8 to Jan 9
    $197 total
    Jan 8 - Jan 9
    Total with taxes and fees
    9.4/10 Exceptional! (234 reviews)
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $244 nightly
    The price is $281 total per night from Jan 8 to Jan 9
    $281 total
    Jan 8 - Jan 9
    Total with taxes and fees
    8.8/10 Excellent! (1,004 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $74 nightly
    The price is $85 total per night from Jan 8 to Jan 9
    $85 total
    Jan 8 - Jan 9
    Total with taxes and fees
    7.8/10 Good! (1,002 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
35 Villas
Lowest Price
$85
Highest Price
$281
Popular accommodation
Hampton Private Retreat - last minute offer June 23-, New Construction Greenport Pool House - 3 Blocks from Town, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Iconic Charles Moore Springs home with dock and our home is pet-friendly, Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA, Villa Direen Modern East Hampton Villa, Villa Flasses, TBD by Rove Travel 7BR Pool Hot Tub, Villa Sofia