Search Condo Rentals in Southold

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 19 Condo Rentals in Southold with updated reviews, rates, and availability.

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

10.0 out of 10, Exceptional, (73)
"The condo was clean and as advertised with an unbelievable view looking over the water with amazing sunsets. We were in Greenport for a Wedding and found the area full of things to do with many wineries and a fun downtown area with restaurants, bars and shopping. Highly recommend the Waterfront Condo for your next visit to Greenport. "
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Elegant Hamptons Hideaway w/ Path to Beach!

6.0 out of 10, (1)
"The property is very well located near the beach and has a nice outdoor area. It's important to know that the three spaces are separate, and the only full bathroom is on the upper floor with external stairs to reach it. Certain things were broken around the property (screen door on the 2nd floor was ripped, not all blinds functioned fully), things that should not be present at this price point."
Elegant Hamptons Hideaway w/ Path to Beach!

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Shelter Island Waterview Villa

Shelter Island Waterview Villa

Million Dollar Sunsets Overlooking Bayfront Beach

Million Dollar Sunsets Overlooking Bayfront Beach

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis

Pools tennis gym golf pickelball

Pools tennis gym golf pickelball

nice condo

nice condo

Beautiful Waterfront Condo

Beautiful Waterfront Condo

Mattituck Marvel

4.0 star property
Mattituck Marvel

Southampton Village Condo

Southampton Village Condo

Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.

Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.

1-bedroom timeshare at Waters Edge Resort & Spa available April 18-25, 2025

1-bedroom timeshare at Waters Edge Resort & Spa available April 18-25, 2025

Happy Days in Hampton Bays

Happy Days in Hampton Bays

Heaven in the Hamptons

Heaven in the Hamptons

Southampton condo close to beach and village

Southampton condo close to beach and village

Amagansett Beachfront Beauty

4.0 star property
Amagansett Beachfront Beauty

Beautiful Beach Front 1 Bedroom Triplex

Beautiful Beach Front 1 Bedroom Triplex
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Southold
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southold

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (151)
"Love love love this place ! Can’t say enough "
The price is SAR 635
SAR 726 total
includes taxes & fees
31 Mar - 1 Apr
The Shoals Suites and Slips

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand

White Blossom House Inn

2.5 star property
10.0 out of 10, Exceptional, (6)
"Charming and cozy. Lovely outside sitting areas."
White Blossom House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.