Southold vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Southold
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold vacation rentals
Stay near Southold's top sights
Other great vacation rentals in Southold
Home in North Fork
Le Petit Cottage Southold NY
Home in North Fork
Gorgeous home with heated gunnite pool!
Guest suite in North Fork
Enjoy a relaxing getaway to the North Fork
Home in North Fork
Secluded Farmhouse - Studio Apartment Style Unit
Rental unit in North Fork
Lovely 2-bedroom apartment in a historic home
Home in North Fork
Designer's Dream - Charming Boathouse
Home in North Fork
North Fork paradise between beaches and vineyards
Cottage in North Fork
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
Other great vacation rentals in Southold
Guest suite in North Fork
Private Suite in a Greenport Historical Townhouse
Cottage in North Fork
Adorable Cottage
Home in North Fork
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in North Fork
Cozy Cottage with Views
Home in North Fork
Beach/Lake house Fireplace & Hot Tub, By Wineries
Home in North Fork
Beachfront Greenport Villa
Loft in Westbrook
Lovely one bedroom studio with on-site parking.
Home in North Fork
Historic Stunner in Heart of Village
Quick stats about vacation rentals in Southold
Total rentals
220 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$100 before taxes and fees
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Southold?
Yes! Work meets play with ease at over 120 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southold?
Four-legged friends are welcome in Southold. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Southold?
Experience the best of Southold with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Southold have a bbq area?
Absolutely! We offer over 80 house rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
Are there Southold house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 house rentals with pools in Southold, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Southold have self check-in?
Absolutely! We offer over 40 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Southold have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have a gym?
Absolutely! We offer over 30 house rentals with a gym in Southold. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Southold?
Southold has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cottage Rentals in Southold?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Martha's Vineyard Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Rentals with pools Southold
- Rentals with a fireplace Southold
- Fitness-friendly rentals Southold
- Rentals with a kayak Southold
- Monthly Rentals Southold
- Family-friendly rentals Southold
- Rentals with outdoor seating Southold
- Pet-friendly rentals Southold
- House rentals Southold
- Kid-friendly rentals Southold
- Rentals with a fire pit Southold
- Beachfront rentals Southold
- Rentals with beach access Southold
- Rentals with a washer and dryer Southold
- Rentals with a patio Southold
- Waterfront rentals Southold
- Rentals with lake access Southold
- Rentals with a hot tub Southold
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes