Holiday rentals in Southold
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Southold
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold holiday rentals
Stay near Southold's top sights
Other great holiday rentals in Southold
Guest favourite
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
Guest favourite
Home in Southold
4.96 out of 5 average rating, 28 reviewsBright Oasis in Beautiful North Fork Wine Country
Guest favourite
Home in Southold
4.92 out of 5 average rating, 13 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Guest favourite
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Guest favourite
Home in Southold
5.0 out of 5 average rating, 27 reviewsGreenport walk to beach & vineyard! Brand new home
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
Guest favourite
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Quick stats about holiday 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
€ 93 before taxes and fees
Destinations to explore
- New City Holiday rentals
- Long Island Holiday rentals
- Martha's Vineyard Holiday rentals
- Newark Holiday rentals
- Montauk Holiday rentals
- Hoboken Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Rentals with pools Southold
- Family-friendly rentals Southold
- Rentals with a firepit Southold
- House rentals Southold
- Pet-friendly rentals Southold
- Fitness-friendly rentals Southold
- Monthly Rentals Southold
- Rentals with a kayak Southold
- Rentals with outdoor seating Southold
- Beachfront rentals Southold
- Waterfront rentals Southold
- Family-friendly rentals Southold
- Rentals with lake access Southold
- Rentals with a hot tub Southold
- Rentals with beach access Southold
- Rentals with a washing machine and dryer Southold
- Rentals with a patio Southold
- Rentals with a fireplace 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