
Vacation rentals in Southold
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Top-rated vacation rentals in Southold
Guests agree: these stays 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
Other great vacation rentals in Southold

Private Suite in a Greenport Historical Townhouse

Cozy beach house

Summer Retreat at the beach , enjoy Wine Country

Charming Farmhouse with Pool, Yard, and Walkable

Oak Street Cottage

Southold- Adorable 1 Bedroom Cottage

Sweeping Dunes Beach Cottage

Modern farmhouse w/ pool, beach, horses and winery
Quick stats about vacation rentals in Southold
Total rentals
260 properties
Nightly prices starting at
R1,603 ZAR before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
220 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
90 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Southold?
Yes! Work meets play with ease at over 130 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 apartment rentals in Southold?
Experience the best of Southold with our apartment rentals, starting at about $110 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 condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 condo 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 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 170 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 180 homes with wifi, over 50 homes with self check-in, over 80 homes with a bbq area, over 30 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Rentals with a hot tub Southold
- Rentals with a patio Southold
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- Rentals with beach access Southold
- Kid-friendly rentals Southold
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- House rentals Southold
- Pet-friendly rentals Southold
- Rentals with pools Southold
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- Family-friendly rentals Southold
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- Beach
- Charlestown Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Ocean Beach Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Blue Shutters Beach
- Ninigret Beach
- Silver Sands Beach
- Amagansett Beach
- Groton Long Point Main Beach
- Sunken Meadow State Park
- Seaside Beach
- South Jamesport Beach
- Sandy Beach
- Sherwood Island State Park