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
Cottage in Southold
4.89 out of 5 average rating, 19 reviewsQuaint Cottage Close to LI Sound
Mar 9 – 16
Cottage in Southold
4.95 out of 5 average rating, 21 reviewsAdorable Cottage
Nov 10 – 17
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
Oct 8 – 15
Home in Cutchogue
4.96 out of 5 average rating, 74 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Dec 17 – 24
Home in Southold
4.96 out of 5 average rating, 26 reviewsBright Oasis in Beautiful North Fork Wine Country
Dec 10 – 17
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Jun 3 – 10
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun 11 – 18
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
Mar 15 – 22
Other great vacation rentals in Southold
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Oct 25 – Nov 1
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Oct 20 – 27
Home in Mattituck
4.92 out of 5 average rating, 92 reviewsModern Farmhouse Steps to Beach & Love Lane
Mar 11 – 18
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Sep 1 – 8
Home in Greenport
4.96 out of 5 average rating, 25 reviewsWater front 3 bedrooms 2 bathrooms beach house
Nov 17 – 24
Apartment in Greenport
4.78 out of 5 average rating, 46 reviews2 Bedroom Greenport Waterfront Coastal Cottage
Aug 30 – Sep 6
Loft in Southold
5.0 out of 5 average rating, 12 reviewsEntire Loft-Walk to Town, Beach, Train, Wine Trail
Jan 29 – Feb 5
Home in Peconic
5.0 out of 5 average rating, 11 reviewsCoastal Cottage on the Water
Oct 17 – 24
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
G$20,896 GYD 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.
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 cottage rentals in Southold have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
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 cottage rentals in Southold?
Southold has more than 10 family-friendly cottage 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 wifi, over 10 homes with a bbq area, 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
- Family-friendly rentals Southold
- House rentals Southold
- Rentals with a fire pit Southold
- Rentals with a kayak Southold
- Rentals with a patio Southold
- Kid-friendly rentals Southold
- Rentals with outdoor seating Southold
- Rentals with a hot tub Southold
- Waterfront rentals Southold
- Rentals with a fireplace Southold
- Fitness-friendly rentals Southold
- Rentals with pools Southold
- Monthly Rentals Southold
- Rentals with a washer and dryer Southold
- Beachfront rentals Southold
- Rentals with beach access Southold
- Rentals with lake access Southold
- Pet-friendly rentals Southold
- 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