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 Southold
5.0 out of 5 average rating, 12 reviewsGorgeous home with heated gunnite pool!
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Cottage in Southold
4.95 out of 5 average rating, 21 reviewsAdorable Cottage
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Loft in Southold
5.0 out of 5 average rating, 12 reviewsPrivate Apt & Walk to Town/Beach/Train/Wine/Farms
Home in Southold
4.92 out of 5 average rating, 13 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
Home in Southold
4.96 out of 5 average rating, 28 reviewsBright Oasis in Beautiful North Fork Wine Country
Other great vacation rentals in Southold
Home in Cutchogue
4.96 out of 5 average rating, 76 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Home in Mattituck
4.92 out of 5 average rating, 92 reviewsModern Farmhouse Steps to Beach & Love Lane
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in Cutchogue
5.0 out of 5 average rating, 25 reviewsNorth Fork paradise between beaches and vineyards
Home in Greenport
5.0 out of 5 average rating, 10 reviewsCharming Home W/ Beach & Dock Access
Apartment in Greenport
4.97 out of 5 average rating, 62 reviewsLovely 2-bedroom apartment in a historic home
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 house rentals in Southold?
Experience the best of Southold with our house 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 90 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 50 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have wifi?
Absolutely! We offer over 170 house 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 House Rentals in Southold?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a gym, over 90 homes with a bbq area, over 170 homes with wifi, over 50 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Martha's Vineyard Vacation rentals
- Newark 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 hot tub Southold
- Pet-friendly rentals Southold
- Family-friendly rentals Southold
- Rentals with outdoor seating Southold
- Rentals with a patio Southold
- Rentals with a washer and dryer Southold
- Waterfront rentals Southold
- Fitness-friendly rentals Southold
- Rentals with beach access Southold
- House rentals Southold
- Monthly Rentals Southold
- Kid-friendly rentals Southold
- Beachfront rentals Southold
- Rentals with a fireplace Southold
- Rentals with lake access Southold
- Rentals with a fire pit Southold
- Rentals with a kayak 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