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Southold Villas Guide

Escape to tranquil Southold, where luxurious villas meet Long Island's North Fork charm.

Villas in Town of Southold

Sunsets and Rose by the Pond
£2013  night
6
4
4
Details View Offers
East Hampton Oasis with Pool
£1552  night
7
4
4
Details View Offers
Iconic Charles Moore Springs home with dock and our home is pet-friendly
5.0/5
£806  night
6
3
3
Details View Offers
Hampton Private Retreat - last minute offer June 23-
5.0/5
£1241  night
10
5
6
Details View Offers
Historic Hamptons Beach Town 4-Bedroom & Pool
5.0/5
£1054  night
8
4
4
Details View Offers
Exquisite Home l East Hamptons l Pool
£6310  night
14
6
7
Details View Offers
Contemporary Hamptons Getaway
£557  night
6
4
5
Details View Offers
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
£1377  night
12
4
3
Details View Offers
Villa Coastal Bliss
£1720  night
9
5
2
Details View Offers
Villa Sofia: Luxurious Retreat in East Hampton North
£1720  night
12
6
3
Details View Offers
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
5.0/5
£1287  night
12
4
3
Details View Offers
Live on the Water: Dock, Beach, Boat, Kayak & Fish
5.0/5
£1129  night
9
7
2
Details View Offers
Villa Vajra
£1720  night
8
4
4
Details View Offers
New Construction Greenport Pool House - 3 Blocks from Town
£707  night
16
4
5
Details View Offers
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
£2151  night
10
5
7
Details View Offers
Villa Charlotte
£3440  night
14
7
6
Details View Offers
Amagansett Dunes Luxury wAmagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach/ Pool + Elevator + 2 Min walk to private beach
£5787  night
10
5
6
Details View Offers
Villa Spectrum
£764  night
4
2
2
Details View Offers
Villa Baloch
£1377  night
6
3
3
Details View Offers
Beautiful Mediterranean villa
5.0/5
£1582  night
6
4
4
Details View Offers

Why a holiday villa in Town of Southold

Southold is a haven for those seeking a tranquil and luxurious getaway from the hustle and bustle of city life. This charming town on Long Island's North Fork offers an idyllic setting, perfect for relaxing beachside holidays in its beautiful villas.

Imagine waking up to breathtaking sunrises, spending your days lounging by the pool or exploring the scenic countryside, and enjoying romantic evenings with a loved one in a luxurious villa surrounded by nature. Whether you're looking to unwind, recharge, or simply experience the best of Long Island's charm, Southold's villas have everything you need for an unforgettable holiday experience.

When to rent a villa in Town of Southold

When it comes to planning your villa holiday in Southold, the timing can greatly impact your experience. The town enjoys a moderate climate, with warm summers and mild winters, making it an ideal destination to visit throughout the year. However, if you're looking for the best time to visit, consider heading to Southold during the spring months (April-May) or autumn (September-October). These periods offer pleasant weather, with average highs in the mid-60s to low 70s Fahrenheit, making them perfect for outdoor activities like hiking, biking, and exploring the local beaches.

Summer is also a great time to visit Southold, with warm weather and long days ideal for beachgoers and water sports enthusiasts. However, if you're looking for a more relaxed atmosphere, consider avoiding July and August when the town can get busier with tourists. Winters in Southold are generally mild, with average highs in the mid-40s to low 50s Fahrenheit, making it an excellent time to visit if you prefer cooler weather and don't mind the possibility of some rain. Whatever the season, Southold's villas offer a comfortable and luxurious retreat from the elements.

Where to go in Town of Southold

When it comes to choosing the perfect location for your villa holiday in Southold, consider heading to the town's scenic waterfront area. This picturesque spot offers stunning views of the Long Island Sound, making it an ideal spot for a relaxing beachside retreat. You can spend your days lounging on the beach, taking leisurely walks along the shore, or exploring the local restaurants and shops that line the water's edge.

For those looking for a more vibrant atmosphere, head to the nearby town center, where you'll find a range of great restaurants, bars, and cafes serving up delicious local cuisine. However, if it's peace and quiet you're after, consider staying in one of Southold's many secluded neighborhoods, where villas are surrounded by lush gardens and rolling countryside. Whatever your preference, Southold has something for everyone, making it the perfect destination for a villa holiday in the United States.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
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Villas in Town of Southold

Sunsets and Rose by the Pond
£2013  night
6
4
4
Details View Offers
East Hampton Oasis with Pool
£1552  night
7
4
4
Details View Offers
Iconic Charles Moore Springs home with dock and our home is pet-friendly
5.0/5
£806  night
6
3
3
Details View Offers
Hampton Private Retreat - last minute offer June 23-
5.0/5
£1241  night
10
5
6
Details View Offers
Historic Hamptons Beach Town 4-Bedroom & Pool
5.0/5
£1054  night
8
4
4
Details View Offers
Exquisite Home l East Hamptons l Pool
£6310  night
14
6
7
Details View Offers
Contemporary Hamptons Getaway
£557  night
6
4
5
Details View Offers
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
£1377  night
12
4
3
Details View Offers
Villa Coastal Bliss
£1720  night
9
5
2
Details View Offers
Villa Sofia: Luxurious Retreat in East Hampton North
£1720  night
12
6
3
Details View Offers
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
5.0/5
£1287  night
12
4
3
Details View Offers
Live on the Water: Dock, Beach, Boat, Kayak & Fish
5.0/5
£1129  night
9
7
2
Details View Offers
Villa Vajra
£1720  night
8
4
4
Details View Offers
New Construction Greenport Pool House - 3 Blocks from Town
£707  night
16
4
5
Details View Offers
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
£2151  night
10
5
7
Details View Offers
Villa Charlotte
£3440  night
14
7
6
Details View Offers
Amagansett Dunes Luxury wAmagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach/ Pool + Elevator + 2 Min walk to private beach
£5787  night
10
5
6
Details View Offers
Villa Spectrum
£764  night
4
2
2
Details View Offers
Villa Baloch
£1377  night
6
3
3
Details View Offers
Beautiful Mediterranean villa
5.0/5
£1582  night
6
4
4
Details View Offers