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Holiday homes in Southold You’ll Love

Top-Rated Southold Holiday homes for Every Budget and Style!

Looking for a holiday home in Southold (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Southold.

We found 24 Holiday-homes in Southold and the surrounding area (within 30 miles)

Villa Ebrar - Luxury with pool in Sag Harbor, USA

Villa Ebrar - Luxury with pool

Villa in Sag Harbor near Southold, Florida , 16 Noyack Harbor Road
Featuring free bikes, Villa Ebrar - Luxury with pool features accommodations in Sag Harbor.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Indoor pool

Exceptional 1 Reviews 10.0

from $3.480.04 Show details »

Water-View New Suffolk Cottage on North Fork! in New Suffolk, USA

Water-View New Suffolk Cottage on North...

Holiday home in New Suffolk near Southold, Florida
The air-conditioned accommodation is 16 miles from Splish Splash.
  • Parking
  • Pets allowed

no reviews

from $92.00 Show details »

Enchanting North Fork Garden Cottage with Water View in New Suffolk, USA

Enchanting North Fork Garden Cottage wit...

Holiday home in New Suffolk near Southold, Florida
The air-conditioned accommodation is 16 miles from Splish Splash.
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $53.00 Show details »

Home in Long Island Wine Country - Walk to Beach! in Cutchogue, USA

Home in Long Island Wine Country - Walk...

Holiday home in Cutchogue near Southold, Florida
Home in Long Island Wine Country - Walk to Beach! is located in Cutchogue, just a 12-minute walk from Fleet Neck Beach and 20 miles from Splish Splash...
  • Parking
  • Spa and wellness centre

no reviews

from $61.00 Show details »

The Endless Summer Cottage in Cutchogue, USA

The Endless Summer Cottage

Holiday home in Cutchogue near Southold, Florida
The Endless Summer Cottage offers accommodations in Cutchogue, 1.8 miles from Fisherman Beach and 1.8 miles from Fleet Neck Beach.
  • Parking

Exceptional 1 Reviews 10.0

from $79.00 Show details »

Historic North Fork Farmhouse Near Wineries! in Cutchogue, USA

Historic North Fork Farmhouse Near Winer...

Holiday home in Cutchogue near Southold, Florida
The air-conditioned accommodation is 16 miles from Splish Splash.
  • Parking

no reviews

from $98.00 Show details »

Watersedge Retreat in Southold, USA

Watersedge Retreat

Holiday home in Southold, Florida
Watersedge Retreat offers accommodations in Southold, 1.7 miles from Cedar Beach County Park and 23 miles from Splish Splash.
  • Parking

no reviews

from $55.00 Show details »

Minnehaha Marvel in Southold, USA

Minnehaha Marvel

Holiday home in Southold, Florida
Offering a garden, Minnehaha Marvel offers accommodations in Southold.
  • Pets allowed

no reviews

from $80.00 Show details »

Southold Cottage with Deck and Grill - Walk to Beach in Southold, USA

Southold Cottage with Deck and Grill - W...

Holiday home in Southold, Florida
Free Wifi is available throughout the property and Splish Splash is 21 miles away.
  • Parking

no reviews

from $50.00 Show details »

Southold Serenity in Southold, USA

Southold Serenity

Holiday home in Southold, Florida
Southold Serenity offers accommodations in Southold, 23 miles from Splish Splash.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $88.00 Show details »

Bright Oasis in Beautiful North Fork Wine Country in Southold, USA

Bright Oasis in Beautiful North Fork Win...

Holiday home in Southold, Florida , 3795 Main Bayview Road
Bright Oasis in Beautiful North Fork Wine Country offers accommodations in Southold, 21 miles from Splish Splash.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $89.00 Show details »

Secret Garden Estate in Southold, USA

Secret Garden Estate

Holiday home in Southold, Florida
Guests are welcome to go for a swim in the private pool.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $73.00 Show details »

Classic Southold Country Charmer in Southold, USA

Classic Southold Country Charmer

Holiday home in Southold, Florida
Featuring a garden, Classic Southold Country Charmer offers accommodations in Southold.
  • Parking

Exceptional 1 Reviews 10.0

from $64.00 Show details »

Waterfront Southold Retreat Less Than 3 Mi to Wineries! in Southold, USA

Waterfront Southold Retreat Less Than 3...

Holiday home in Southold, Florida
The air-conditioned accommodation is 22 miles from Splish Splash.
  • Parking
  • Spa and wellness centre

no reviews

from $62.00 Show details »

Sea Breeze Paradise: Beachfront & Panoramic Views in Southold, USA

Sea Breeze Paradise: Beachfront & Panora...

Holiday home in Southold, Florida , 20845 Soundview Ave
Sea Breeze Paradise: Beachfront & Panoramic Views offers accommodations in Southold, 22 miles from Splish Splash.
  • Fitness centre

no reviews

from $53.00 Show details »

Modern on 9th in Greenport, USA

Modern on 9th

Holiday home in Greenport near Southold, Florida
Providing a garden, Modern on 9th features accommodations in Greenport.
  • Parking
  • Pets allowed

no reviews

from $66.00 Show details »

Greenport Village Vacationers Delight in Greenport, USA

Greenport Village Vacationers Delight

Holiday home in Greenport near Southold, Florida
Free Wifi is available throughout the property and Splish Splash is 26 miles away.
  • Parking
  • Pets allowed

no reviews

from $55.00 Show details »

Cozy Greenport Cottage in Greenport, USA

Cozy Greenport Cottage

Holiday home in Greenport near Southold, Florida
Providing a garden, Cozy Greenport Cottage provides accommodations in Greenport.
  • Parking
  • Sauna
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $69.00 Show details »

Renovated and Spacious Summer Home with Water View in Greenport, USA

Renovated and Spacious Summer Home with...

Holiday home in Greenport near Southold, Florida , 71 Gardiners Bay Drive
Renovated and Spacious Summer Home with Water View offers accommodations in Greenport, a 1-minute walk from Hay Beach.
  • Parking
  • Pets allowed

no reviews

from $63.00 Show details »

Family and Friends in Historic Greenport House in Greenport, USA

Family and Friends in Historic Greenport...

Holiday home in Greenport near Southold, Florida , 636 2nd Street
Featuring a garden, Family and Friends in Historic Greenport House offers accommodations in Greenport.
  • Parking
  • Pets allowed

no reviews

from $60.00 Show details »

Lavender Bay Breezes - Private Bay Beach Community in East Marion, USA

Lavender Bay Breezes - Private Bay Beach...

Holiday home in East Marion near Southold, Florida
Free Wifi is available throughout the property and Splish Splash is 27 miles away.
  • Parking
  • Pets allowed

no reviews

from $61.00 Show details »

Lagoon Lodge: North Fork,Charming 3Br, Waterfront in East Marion, USA

Lagoon Lodge: North Fork,Charming 3Br, W...

Holiday home in East Marion near Southold, Florida , 270 Knoll Circle
The air-conditioned accommodation is 28 miles from Splish Splash, and guests can benefit from on-site private parking and complimentary Wifi.
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $86.00 Show details »

Lavender Fields Retreat: Nearby the Beach & Farms in East Marion, USA

Lavender Fields Retreat: Nearby the Beac...

Holiday home in East Marion near Southold, Florida , 65 Bayview Drive
The air-conditioned accommodation is 28 miles from Splish Splash.
  • Fitness centre

no reviews

from $71.00 Show details »

Victorian Seasons Cape in East Marion, USA

Victorian Seasons Cape

Holiday home in East Marion near Southold, Florida , 8485 Main Road
Victorian Seasons Cape offers accommodations in East Marion, 27 miles from Splish Splash.
  • Parking
  • Family rooms

no reviews

from $76.00 Show details »

Number of Holiday homes in Southold 24
Number of guest ratings 88
Average price per night $804.00
Lowest price per night $50,00
Highest price per night $12.137,00

Top 10 Cheapest Holiday-homes in Southold

Discover the Cheapest Holiday-homes in Southold – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Southold

Check out the Most Booked Holiday-homes in Southold – Based on Guest Popularity.

Holiday homes in Southold (Florida), comfortable and familiar

Staying in a holiday or vacation home in Southold can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Southold for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Southold should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com