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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 18 Condo Rentals in Southold with updated reviews, rates, and availability.

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

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

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
Shelter Island Waterview Villa
Property grounds

Shelter Island Waterview Villa

Shelter Island Waterview Villa
nice condo
Interior

nice condo

nice condo
Elegant Hamptons Hideaway w/ Path to Beach!
1 bedroom, iron/ironing board, internet, bed sheets

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!
Million Dollar Sunsets Overlooking Bayfront Beach
Outdoor pool, a heated pool

Million Dollar Sunsets Overlooking Bayfront Beach

Million Dollar Sunsets Overlooking Bayfront Beach
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, outdoor pool

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

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

Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.
Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Beach

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

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Pools tennis gym golf pickelball
A heated pool

Pools tennis gym golf pickelball

Pools tennis gym golf pickelball
Beautiful Waterfront Condo
Living area

Beautiful Waterfront Condo

Beautiful Waterfront Condo
Mattituck Marvel
House, Multiple Beds (Mattituck Marvel) | Balcony

Mattituck Marvel

4.0 star property
Mattituck Marvel
Southampton Village Condo
A heated pool

Southampton Village Condo

Southampton Village Condo
Happy Days in Hampton Bays
Fridge, microwave, oven, stovetop

Happy Days in Hampton Bays

Happy Days in Hampton Bays
Southampton condo close to beach and village
Outdoor dining

Southampton condo close to beach and village

Southampton condo close to beach and village
Heaven in the Hamptons
Pool

Heaven in the Hamptons

Heaven in the Hamptons
Amagansett Beachfront Beauty
House, Multiple Beds (Amagansett Beachfront Beauty) | 4 bedrooms

Amagansett Beachfront Beauty

4.0 star property
Amagansett Beachfront Beauty
Beautiful Beach Front 1 Bedroom Triplex
Beach

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
Sign in
Sign up, it's free

Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape
Beach nearby

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
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is AED 484
AED 633 total
includes taxes & fees
31 Mar - 1 Apr
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is AED 636
AED 887 total
includes taxes & fees
28 Apr - 29 Apr
Cliffside Resort Condominiums
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.