107 Southold Holiday Rentals

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Compare Southold holiday rentals from 10 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $57 to $8471 a night.

Information about Southold

Vacation Rentals in Southold

Find the best Southold vacation rentals with Tripping.com. Choose from 877 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $57 a night to $8471 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 720 of homes in Southold offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 337 rentals with pool or jacuzzi, or relax with the family in one of the 689 homes with cable TV.

For all those dog lovers and cat lovers, Southold offers 318 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 10 rental sites in Southold where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 713 HomeAway rentals, 93 TripAdvisor short term rentals and 37 Booking.com vacation rentals.