Condo vacation rentals in Southold

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Popular amenities for Southold condo rentals

Weekly condo rentals

Superhost
A fully equipped kitchen features stainless steel appliances, including a refrigerator and range. Granite countertops provide ample workspace, and a window allows natural light to illuminate the area. A small dining space is visible near the sink, enhancing functionality.
Condo in Wooster Square
4.84 out of 5 average rating, 286 reviews

Stunning, Spacious, Spotless. Close to Yale.

DaltonRating, 5 stars2 weeks ago
Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.
Superhost
A rocky shoreline is viewed, with the vibrant blue ocean stretching into the horizon. Waves gently lap against the weathered stone, showcasing a natural pattern of colors in the rock. A partly cloudy sky casts soft light across the water's surface.
Condo in Old Lyme
4.91 out of 5 average rating, 32 reviews

The Anchor at Soundview · Beach+Ocean+Sunrise

JeffreyRating, 5 stars2 weeks ago
Great! Met our needs of staying somewhere for a couple of nights while visiting the area. Just be aware that there are not that many restaurants and shops in the immediate vicinity so you may need to go to towns 30 or so minutes away.
Superhost
A sandy beach stretches along the Long Island Sound, bordered by greenery. A wooden boardwalk leads to the shore, with lounge chairs positioned for sunbathing. In the background, several buildings are nestled among the trees, completing the tranquil seaside scene.
Condo in North Fork
4.85 out of 5 average rating, 136 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

SeanRating, 5 stars3 weeks ago
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.
Superhost
A bright living area is showcased with soft carpeting and wooden beams along the ceiling. A white dining table and chairs are featured, with a kitchenette in view. Sunlight streams through a skylight and large windows, illuminating the space.
Condo in The Hamptons
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars56 months ago
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.
Superhost
A light-filled hallway features smooth, polished wooden flooring extending towards open doorways. Neutral-colored walls are complemented by a small decorative plant placed on a white side table. A framed artwork hangs on the wall, adding subtle detail to the space.
Condo in Old Saybrook
4.89 out of 5 average rating, 74 reviews

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.
Superhost
An open-concept kitchen and living area features a central island with bar seating, surrounded by modern appliances and white cabinetry. Natural light pours in through large windows, illuminating a cozy seating area with a sofa and dining space, creating a welcoming environment.
Condo in The Hamptons
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars9 months ago
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+
Superhost
A private beach stretches along the coastline, with soft sand and patches of greenery. A wooden pathway leads from the grassy area to the water, while several beach loungers are positioned facing the shore. The gentle waves of Long Island Sound meet the sandy beach under a clear sky.
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars1 month ago
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!
Superhost
An open-concept living area features a round dining table surrounded by four wooden chairs. A comfortable green sofa is positioned adjacent, facing a wall-mounted television. A kitchenette is visible in the background, equipped with essential appliances and utensils, set against light-colored cabinetry.
Condo in The Hamptons
4.9 out of 5 average rating, 81 reviews

Cute cottage apartment upstairs in Sag

DarinaRating, 5 stars3 weeks ago
We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.

Condo rentals with a pool

Lounge chairs are arranged around a patio area, each shaded by a large umbrella. A potted plant adds a touch of greenery, and a serene body of water is visible in the background, bordered by lush vegetation and a wooden fence.
Condo in The Hamptons

One Bedroom Apartment Nestled in the Dunes

AlecRating, 5 stars35 months ago
if you are looking for private, quiet, tranquil, beautiful, relaxing stay. This is the place. Private beach with comfy chairs, umbrellas, amazing pool and views, felt like a nature preserve. Walk to town. Apartment was great. I'll be back
A bright living area is furnished with a light-colored sofa, floral-patterned chairs, and a coffee table with decorative items. A large television is positioned on a dark wooden console. Natural light filters in through windows, illuminating the space with a cozy ambiance.
Condo in The Hamptons

Charming Bayfront Condo

SaraRating, 5 stars9 months ago
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.
Superhost
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars1 month ago
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!
The living area features a comfortable seating arrangement with a dark couch and light-colored accent chairs. A dining table sits nearby, accompanied by additional seating. Large windows offer natural light, with greenery visible outside. A flat-screen TV and decorative mirror add to the space.
Condo in North Fork
4.8 out of 5 average rating, 5 reviews

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo

JoshuaRating, 5 stars5 months ago
Stay was great and the place was very clean
A well-maintained exterior features a spacious patio area, bordered by manicured flower beds and shrubs. The multi-panel front doors provide an inviting entrance, while the grey shingle siding complements the home's architecture. Bright sunlight enhances the natural colors of the outdoor space.
Condo in Westbrook

Watersedge resort time share Westbrook ct

AbbieRating, 5 stars49 months ago
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.
A spacious outdoor pool is surrounded by comfortable lounge chairs. The clear blue water reflects the sunlight under a clear sky. The condo building features multiple balconies overlooking the pool area, enhancing the inviting atmosphere for relaxation and leisure.
Condo in North Fork
4.84 out of 5 average rating, 31 reviews

Two Bedroom Lawn Side 1st Floor Condo!

RaeMarieRating, 5 stars35 months ago
This was a wonderful place to stay. Clean and just beautiful. The condo and the scenery. My family and I truly enjoyed our short stay. Only one night. Looking forward to coming again and spending more time
A heated swimming pool is surrounded by lounge chairs, with a view of the multi-story condominium units in the background. The pool’s clear water reflects the blue sky above, and established landscaping adds a touch of greenery along the perimeter.
Condo in North Fork
5 out of 5 average rating, 3 reviews

Cliffside Resort Poolside Condo A105

KathleenRating, 5 stars9 months ago
Beautiful stay at Cliffside! The photos don’t do it any justice!! The rooms were super clean and well decorated. Pool was great!! The beach was beautiful!!!! Loved this place!
A bright, open living area features a large sectional sofa and a unique coffee table with fringe detailing. Large windows allow natural light to fill the space, offering views of the ocean beyond. The tile floor adds a fresh, clean aesthetic to the room.
Condo in The Hamptons

Oceanfront Condo w/ Spectacular View Furnished

Private condo rentals

A modern bathroom is displayed, featuring a sleek vessel sink atop a minimalist white cabinet. The shower area includes glass walls and a handheld showerhead, with light-colored wood panels complementing the dark stone flooring. Natural light is welcomed through a small window.
Condo in The Hamptons

Bright and Airy One Bedroom Apartment in the Dunes

TimRating, 5 stars21 months ago
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!
Superhost
A rocky shoreline is viewed, with the vibrant blue ocean stretching into the horizon. Waves gently lap against the weathered stone, showcasing a natural pattern of colors in the rock. A partly cloudy sky casts soft light across the water's surface.
Condo in Old Lyme
4.91 out of 5 average rating, 32 reviews

The Anchor at Soundview · Beach+Ocean+Sunrise

JeffreyRating, 5 stars2 weeks ago
Great! Met our needs of staying somewhere for a couple of nights while visiting the area. Just be aware that there are not that many restaurants and shops in the immediate vicinity so you may need to go to towns 30 or so minutes away.
Guest favorite
A street view captures a charming brick building with large windows, marked SSMM, alongside a restaurant displaying Italian flags. Lush green trees line the sidewalk, and a crosswalk is visible, enhancing pedestrian accessibility. Bright blue skies create a welcoming atmosphere.
Condo in Wooster Square
4.93 out of 5 average rating, 29 reviews

Cozy one bedroom apartment in Wooster street

Ana LuizaRating, 5 stars14 months ago
Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!
A beachfront area is shown, featuring a pathway leading from a grassy hill to the sandy shore. Multiple lounge chairs are arranged neatly on the beach, with a view of a multistory condominium building in the background.
Condo in North Fork

Cliffside Resort Poolside Condo A106

KellyRating, 5 stars43 months ago
Very lovely place to stay. All the amenities you would need and a view of the water. With the exception of the keypad entry not working at the end of our stay (assuming it was just dead batteries), it was wonderful.
An open concept living area features a modern kitchen with a dark granite countertop and stainless steel appliances. A spacious living room showcases a large blue sofa and built-in bookshelves, with a decorative clock and artwork adorning the walls. Natural light fills the space.
Condo in The Hamptons

Sun Drenched Loft-City Living in the Country

SusanRating, 5 stars21 months ago
This place is great in old-school AirBnB style. Feels like Nadine’s second home being shared with us. Quality finishes throughout, very well stocked in terms of glasses, plates, towels, etc. We came for a wedding but were able to have our own nuclear family reunion with three young-adult children coming in from around the country. The space handled us all with ease. The great room is spacious with a big table and even bigger sectional sofa. Just a great place to gather and hang out (which we did a little more than expected because of tropical storm Ophelia). We enjoyed the coffee and sandwiches across the street and brought in sushi and wine for one dinner, less than 5 minutes drive away. One quick note: 2 BRs not 3
Superhost
The image captures a rocky shoreline, showcasing smooth, multicolored rock formations with shades of brown and gray. The ocean gently laps against the rocks, reflecting a bright blue sky dotted with white clouds. The calm waters extend into the horizon, creating a serene coastal vista.
Condo in Old Lyme
4.47 out of 5 average rating, 17 reviews

Freeboard at Soundview · Beach+Ocean+Sunrise

HelemahRating, 5 stars1 day ago
This was a great place to reset. I will say, don't get intimidated when you 1st walk in. The floors are a bit wonky and the walls are very thin. But I never felt more at home than when I saw my space. The neighbors were so friendly and the walk to the beach was about a block. Though it was cold we truly enjoyed the beach. And walked down there multiple times a day. There is also a gas station and convenience store 3min driving and very walkable.
Guest favorite
Condo in Old Lyme
4.89 out of 5 average rating, 35 reviews

Hatch at Soundview · Beach+OceanView+Sunrise

RyanRating, 5 stars1 week ago
We had a pleasant time at Peter's place. He was a great host and was very responsive. It was just what we needed for some rest and relaxation on the beach after a week of hiking in the white mountains. Would definitely stay here again!
Guest favorite
Condo in Old Lyme
4.94 out of 5 average rating, 16 reviews

The Bridge at Soundview · Beach+OceanView+Sunrise

JocelynRating, 5 stars1 month ago
This was such a beautiful place. I was surprised with how much space there was. Me and my family very much enjoyed our stay.

Quick stats about condo rentals in Southold

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$25,097 GYD 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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