Apartment vacation rentals in Southampton

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Top-rated apartment rentals in Southampton

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Guest favorite

Apartment in Sag Harbor

4.94 out of 5 average rating, 136 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

Aug 22 – 29

G$138,514 GYD per night

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Nov 15 – 22

G$62,478 GYD per night

Guest favorite

Apartment in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly, artists apartment & guest cabin.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach. Centrally located. Free bikes, surf boards, 3 stand up paddle boards and a large canoe. Minutes from most beaches. A shaded, fenced in dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. Used if you bring more guests or if the two primary guests require separate rooms. WIFI AC and heat but No bathroom in the cabin.

Oct 17 – 24

G$105,783 GYD per night

Guest favorite

Apartment in East Hampton

4.95 out of 5 average rating, 128 reviews

Comfy Studio

Entire second story studio apartment with private entrance, only a 5 min drive to East Hampton Town, surrounded by nature in a family friendly neighborhood. Very nice to rest or just a get away from the city. 10 minutes away from many beaches (Main Beach, Indian Wells, Maidstone, Atlantic...). Many shops and restaurants in towns. The Montauk Light house is just a 30min drive away. We can also provide some other things to use out here please feel free to ask. Owner lives on the property.

Sep 4 – 11

G$64,416 GYD per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 133 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Oct 7 – 14

G$71,953 GYD per night

Guest favorite

Apartment in Southold

4.96 out of 5 average rating, 100 reviews

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Sep 16 – 23

G$61,050 GYD per night

Guest favorite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Sep 22 – 29

G$59,243 GYD per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Sep 24 – Oct 1

G$155,811 GYD per night

Guest favorite

Apartment in Sag Harbor

4.88 out of 5 average rating, 134 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.

Aug 11 – 18

G$80,608 GYD per night

Guest favorite

Apartment in Montauk

4.91 out of 5 average rating, 199 reviews

Montauk Beach Bungalow West

Inquire about discounts for monthly bookings. Charming, clean, private, quiet, 2 bed one bath ocean view apartment 500 feet from door to ocean beach through lovely dunes. Dine inside or out with view of the moon rising over the breaking waves. Includes BBQ and fire pit. Full kitchen with stove, oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc. -

Oct 23 – 30

G$71,681 GYD per night

Guest favorite

Apartment in Southampton

4.96 out of 5 average rating, 166 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Jul 20 – 27

G$102,117 GYD per night

Guest favorite

Apartment in Rocky Point

4.93 out of 5 average rating, 123 reviews

North shore Guest Room.

This apartment is our guest room with outside private entrance and off street parking. Apartment has a refrigerator, microwave, coffee maker, and toaster oven. Queen bed and a twin pullout couch bed is provided. The place is appropriate for a short stay as an affordable alternative to hotel stay.

Jun 3 – 8

G$23,568 GYD per night