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Apartment vacation rentals in Southampton

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Top-rated apartment rentals in Southampton

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Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Rental unit in Sag Harbor

4.89 out of 5 average rating, 138 reviews

Whaling Captain Pierson's Apartment

Whaling Captain Pierson's Apartment is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment TOO and Whaling Captain Pierson's Cottage).

Rental unit in North Fork

4.96 out of 5 average rating, 140 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)

Rental unit in Sag Harbor

4.99 out of 5 average rating, 159 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!

Rental unit in Westhampton Beach

4.94 out of 5 average rating, 104 reviews

NEW, steps to the village 1 mile to Dune Road

Newly renovated, spacious apartment with separate entrance, on picturesque tree lined street This quaint space is steps from Main street, Farmer's Market, 1 mile to famous Hamptons Beaches. Numerous restaurants and shops are a short walk away. 42 inch HD TV with Chrome Cast for streaming TV and movies . Kitchenette stocked with all new dinner ware, glassware, coffee maker, microwave, toaster oven (no stove). We are COVID-19 compliant, wiping down all surfaces between guests.

Rental unit in Hampton Bays

4.97 out of 5 average rating, 104 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

Rental unit in Southampton

4.95 out of 5 average rating, 192 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

Rental unit in Shelter Island Heights

4.91 out of 5 average rating, 245 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Rental unit in North Fork

4.82 out of 5 average rating, 119 reviews

House on First

This beautiful upstairs apartment is 2 blocks from the charming Village of Greenport. It’s walking distance to many fine restaurants, beautiful beaches, antique carousel in Mitchell Park and ferry to Shelter Island. There’s a deck upstairs you can have your morning coffee before you head out on your next adventure!

Rental unit in Southampton

4.87 out of 5 average rating, 127 reviews

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

Rental unit in North Fork

4.97 out of 5 average rating, 232 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Southampton apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in Southampton

5 out of 5 average rating, 6 reviews

Sugarloaf Annex

Rental unit in Amagansett

4.67 out of 5 average rating, 3 reviews

Fresh&Crisp 1BR w/Loft, Corner Unit + Amazing View

Rental unit in Montauk

5 out of 5 average rating, 9 reviews

Guest Suite in Montauk

Rental unit in Shirley

4.93 out of 5 average rating, 71 reviews

Boho Beach Vibez Retreat! Private entrance

Rental unit in Montauk

4.93 out of 5 average rating, 80 reviews

Montauk’s Secret Private Spot

Rental unit in Sag Harbor

4.69 out of 5 average rating, 55 reviews

Sag Harbor Suite by the Beach

Rental unit in Montauk

4.79 out of 5 average rating, 28 reviews

Montauk Ocean View One Bedroom

Rental unit in North Fork

4.93 out of 5 average rating, 92 reviews

BoHoBayStay: ground floor apt, patio, beach access

Private apartment rentals

Rental unit in Montauk

4.94 out of 5 average rating, 87 reviews

Peaceful Montauk.

Rental unit in East Hampton

4.75 out of 5 average rating, 20 reviews

Total Privacy in Springs.

Rental unit in Southampton

4.96 out of 5 average rating, 27 reviews

Beautiful Sunny one bedroom apt in SH. NY.

Rental unit in Hampton Bays

5 out of 5 average rating, 47 reviews

Hampton Studio

Rental unit in Sagaponack

4.95 out of 5 average rating, 63 reviews

Hamptons elegant and comfortable apartment

Rental unit in Sag Harbor

5 out of 5 average rating, 13 reviews

Spacious Apt. Walk to Beach!

Rental unit in Hampton Bays

4.85 out of 5 average rating, 13 reviews

2BR Hampton's Serenity Getaway w/Kayaks and BBQ

Rental unit in Shirley

5 out of 5 average rating, 25 reviews

1 BR Zen Den Apt in Safe & Beautiful Neighborhood

Apartment rentals with a hot tub

Rental unit in Montauk

5 out of 5 average rating, 6 reviews

Updated 4 Bed, 1 Bedroom Waterfront Condo

Rental unit in Rocky Point

4.29 out of 5 average rating, 31 reviews

Beach, Shopping,Wineries, Dining, 2 BR

Rental unit in Hampton Bays

4.96 out of 5 average rating, 45 reviews

Hamptons Beach Cottage w/ infinity pool & hot tub

Rental unit in Montauk

5 out of 5 average rating, 6 reviews

Bayfront Million Dollar Views

Rental unit in Southampton

5 out of 5 average rating, 80 reviews

Private w/Hot tub Fire Pit Coffee Bar

Rental unit in Bridgehampton

4.95 out of 5 average rating, 65 reviews

Studio King in the Hamptons

Quick stats about apartment rentals in Southampton

Total rentals
120 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
450 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore