
Condo vacation rentals in Southold
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Top-rated condo rentals in Southold
Guests agree: these condos are highly rated for location, cleanliness, and more.
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Popular amenities for Southold condo rentals
Weekly condo rentals

The Anchor at Soundview · Beach+Ocean+Sunrise
Nice place, nice people relaxing vibe comfortable bed tons of free movies

Oceanfront Condo – Incredible Spring Rates!
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Waterfront Elevated Bungalow - Spectacular Views
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

Seashore getaway - CT shoreline
Thanks Lauren! We enjoyed your lovely place!

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Oceanfront Condo - Incredible Spring Rates!
My stay at Julie’s was wonderful, I was always able to message and get a quick response she was very accommodating. The view was beautiful and felt comfy like home. I will definitely be returning in the summer once it’s warmer !

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

Hatch at Soundview · Beach+OceanView+Sunrise
Amazing little spot next to the beach ⛱️. The host were super sweet and very responsive to any issues we had. It's just as pretty as it looks in the photos. I had an amazing stay, would definitely stay here again.
Pet-friendly condo rentals

Private Newly built Modern East Hampton Apartment!
We had a great time at Vanessa’s apartment with our dog. Vanessa was always responsive and very helpful along the way. Centrally located between all of the surrounding towns and the apartment had everything you needed! The nature of the complex does allow for some outside noise from neighbors but the apartment complex was very peaceful and well kept. We hope to be back in the summer time to explore more of the beaches!

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Cute cottage apartment upstairs in Sag
Great place to stay in Sag Harbor!

Charming Sag Harbor Condo right in town/Main St!
Condo rentals with a pool

Oceanfront Condo - Incredible Spring Rates!
My stay at Julie’s was wonderful, I was always able to message and get a quick response she was very accommodating. The view was beautiful and felt comfy like home. I will definitely be returning in the summer once it’s warmer !

Newly Renovated Modern Townhouse w/Pool & Tennis

Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
Quick stats about condo rentals in Southold
Total rentals
20 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Sunken Meadow State Park
- Steer's Beach
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