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

Amagansett Beachfront Beauty

4.0 star property
Amagansett Beachfront Beauty

Southampton condo close to beach and village

Southampton condo close to beach and village

Heaven in the Hamptons

Heaven in the Hamptons

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

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is SAR 494
SAR 646 total
includes taxes & fees
10 Mar - 11 Mar
Windward Shores Ocean Resort

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
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.