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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

Orient
With a stay at this villa in Orient Point, you'll be within a 10-minute walk of Orient By The Sea Marina and Orient Point County Park.
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Hampton Bays
With a stay at this villa in Hampton Bays, you'll be within a 15-minute drive of The Hamptons Beaches and All Star Bowling.
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Greenport
The price is AU$1,685 per night from 2 Jan to 3 Jan
AU$1,685
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at this villa, you'll be centrally located in Greenport, just a 4-minute walk from Greenport Farmers' Market and 5 minutes by foot from Railroad ...
New Construction Greenport Pool House - 3 Blocks from Town
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Villa Direen Modern East Hampton Villa

Villa Direen Modern East Hampton Villa

3.5 out of 5
137 Stephen Hands Path, East Hampton, NY
With a stay at this villa in East Hampton (East Hampton North), you'll be a 4-minute drive from The Jewish Center of the Hamptons and 5 minutes from Guild ...
Villa Direen Modern East Hampton Villa
Villa Flasses

Villa Flasses

3 out of 5
94 Spring Pond Ln, Southampton, NY
With a stay at this villa in Southampton, you'll be within a 5-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.
Villa Flasses
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
Located in East Hampton, this villa is on the waterfront, within a 5-minute drive of Three Mile Harbor and The Hamptons Beaches.
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

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach

Montauk
With a stay at this villa in Amagansett (Beach Hampton), you'll be within a 5-minute walk of The Hamptons Beaches and Amagansett Beach.
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound

Riverhead
Located in Riverhead, this villa is within a 5-minute drive of Hallockville Museum Farm and Martha Clara Vineyards.
Luxurious beach house on the Long Island sound
Live on the Water: Dock, Beach, Boat, Kayak & Fish

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

Southampton
Located in Southampton, this villa is on the waterfront, a 4-minute drive from The Hamptons Beaches and 7 minutes from North Main Street Historic District.
Live on the Water: Dock, Beach, Boat, Kayak & Fish
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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.

Southold Luxury Villas

It’s time to plan your next getaway, and this time, you want it to be amazing. You just want a holiday where you’ll come away with humble brags like “I just couldn’t choose between the pool or the hot tub” and “It was so hard for the whole family to pick their rooms in such a big house”. OK, maybe those aren’t so humble. And that’s exactly the point when you’ve got Southold villa accommodation from lastminute.com.au.

You know what else you might get with that villa? A gourmet kitchen. What does one do in a gourmet kitchen? Why, craft delicious meals that are bound to impress your significant other, kiddos, mum, or whoever else you count among your travelling companions. Nothing says “clan getaway” like a tasty dinner in luxey surroundings, after all. But who says you even have to cook? Conjuring up gastronomic delights takes effort, and you ask us, cheap villa holidays are all about relaxing—and enjoying the fact you’re getting so much bang for your buck. Southold has plenty of ways to delight your taste buds, and don’t get us started on the scenery. No filter, indeed.

Yes, this holiday will give you plenty of humble brags, but there’s nothing humble at all about our awesome deals. Put in for some annual leave and grab some pocket change, because we’ve got Southold villas that will have you wondering “How is that even possible?” Anything is possible—well, almost anything—when you’ve got lastminute.com.au on your side.

Southold Villas essential information

Accommodation
44 Villas
Lowest Price
AU$200
Highest Price
AU$1,685
Popular accommodation
1.5 Acre Luxury Escape - Saltwater Pool with Water Views, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, New Construction Greenport Pool House - 3 Blocks from Town, Villa Direen Modern East Hampton Villa, Villa Flasses, 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, Luxurious beach house on the Long Island sound, Live on the Water: Dock, Beach, Boat, Kayak & Fish

Top trending hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is AU$309 per night from 5 Jan to 6 Jan
AU$309
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella ...
The Shoals Suites and Slips
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 15 Jan to 16 Jan
AU$216
includes taxes & fees
15 Jan - 16 Jan 2025
With a stay at Residence Inn by Marriott New York Long Island East End in Riverhead, you'll be within a 15-minute walk of Tanger Outlet Center and Riverhead ...
Residence Inn by Marriott New York Long Island East End
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 1 Jan to 2 Jan
AU$203
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All ...
Hyatt Place Long Island East End
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Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 29 Dec to 30 Dec
AU$200
includes taxes & fees
29 Dec - 30 Dec
A stay at Hilton Garden Inn Riverhead places you in the heart of Riverhead, within a 5-minute drive of Splish Splash Water Park and Out East Family Fun.
Hilton Garden Inn Riverhead
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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.

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^Subject to availability and chosen travel dates.