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
Guesthouse in Southold
4.95 out of 5 average rating, 42 reviewsSouthold- Adorable 1 Bedroom Cottage
Home in Southold
5.0 out of 5 average rating, 19 reviewsLe Petit Cottage Southold NY
Loft in Southold
5.0 out of 5 average rating, 13 reviewsPrivate Loft-Walk to Town/Beach/Train/Wine/Farms
Guest suite in Cutchogue
4.9 out of 5 average rating, 84 reviewsEnjoy a relaxing getaway to the North Fork
Home in Southold
5.0 out of 5 average rating, 17 reviewsGorgeous home with heated gunnite pool!
Home in Greenport
4.98 out of 5 average rating, 86 reviewsDesigner's Dream - Charming Boathouse
Cottage in Southold
4.95 out of 5 average rating, 22 reviewsAdorable Cottage
Apartment in Greenport
4.97 out of 5 average rating, 65 reviewsLovely 2-bedroom apartment in a historic home
Other great vacation rentals in Southold
Home in Southold
5.0 out of 5 average rating, 33 reviewsSalt & Sea House - Near wineries, farms, & beaches
Home in Greenport
5.0 out of 5 average rating, 33 reviewsHistoric Stunner in Heart of Village
Home in Cutchogue
4.96 out of 5 average rating, 80 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Home in Cutchogue
4.97 out of 5 average rating, 32 reviewsCozy Cottage with Views
Cottage in Greenport
4.85 out of 5 average rating, 39 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Home in Greenport
5.0 out of 5 average rating, 4 reviewsQuaint Chalet w/Salt-heated Pool
Home in Southold
4.93 out of 5 average rating, 15 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Home in Mattituck
4.93 out of 5 average rating, 96 reviewsModern Farmhouse Steps to Beach & Love Lane
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.
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- Rentals with a fire pit Southold
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