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19 Homes For Rent in Southold, NY

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$35,000/mo
4 Beds | 4 Baths | 2,400 Sqft
700 Gin Lane, Southold, NY 11971
House For Rent

Accepting applications for Summer 2021. The Perfect Place To Enjoy a North Fork Vacation! Beautiful New Home In Bay Front Community. Open Living Room With Fireplace And Flat Screen Tv. Open Dining Room And Kitchen With Easy Access To Covered Porch, Private Backyard w/ heated salt water inground Pool. Master Bedroom Suite On 1st Floor, Additional Master Suite On 2nd Floor As Well As 2 Additional Bedrooms And Full Bath. Short Walk To A Gorgeous Bay Haven Association Beach Right At The End Of The Street. 2 month min. or MD-LD. June $25,000. July $35,000. Aug-LD $40,000.

$4,500/mo
3 Beds | 3 Baths | -- Sqft
13595 Soundview Avenue, Southold, NY 11971
House For Rent

Newly built two story 3BR, 2.5Ba, hidden away on private road short distance to LI Sound beaches, natural surroundings enhance the rental experience, open floor plan, EIK, Den/TV room, dining /living room, office/playroom on second floor, combo outdoor shower, patio

$18,000/mo
4 Beds | 4 Baths | 1,784 Sqft
870 Bay Home Road, Southold, NY 11971
House For Rent

Southold Waterfront Home with large private sugar sand beach on the open bay. Open plan first floor living / dining room, screened in porch, rear garden covered deck. Fully equipped farmhouse kitchen with all appliances, washer, dryer, large mature garden with specimen trees and vineyard views. Outdoor HC shower. CAC in all bedrooms. Master en-suite. Close to all area attractions - farm stands, vineyards, beach, boating, fishing, golf, fine dining, galleries and boutiques. Easy to reach, hard to leave.

$35,000/mo
5 Beds | 4 Baths | 2,800 Sqft
3693 Pine Neck, Southold, NY 11971
House For Rent

This fabulous waterfront spread features heated waterside pool, sprawling patio surround with Firepit and BBQ area, and Boat Dock! Updated kitchens and baths. Huge waterview guest suite with living area on upper level. Main level waterview ensuite Master, 3 Guest BRs, 2 Dens/Flex Space. Outdoor Shower. Kayaks on site. Bring your own Boat! Don't Miss Out! Summer Fun Awaits!

$3,000/mo
2 Beds | 1 Bath | 1,400 Sqft
3825 S Harbor Road, Southold, NY 11971
House For Rent

Looking for a great place to enjoy the outdoors and all the North Fork has to offer? Look no further than this private 2 bedroom beach ranch situated on over an acre of land. Located approximately 10 houses away from South Harbor Beach/Emerson Park and town, this home's freshly painted interior, newly finished floors, new furniture and expansive deck make this home an ideal vacation spot! The calendar is filling fast, don't miss out!

$35,000/mo
4 Beds | 4 Baths | -- Sqft
122 Hickory Avenue, Southold, NY 11971
House For Rent

Vacation in Paradise in a Luxurious Waterfront Home on Goose Creek. Each Room Invites you with Warmth and Beauty. Enjoy your New In Ground Pool, Entertaining Indoors and Out, Sit by the Fire, Really w/ Relax in the Jacuzzi, Dine Al Fresco, Fish, or Kayak. Gorgeous Custom Kitchen, Generous Living Space, Large Bedrooms, All w/ a Water View. This is Your Dream Vacation!

$30,000/mo
5 Beds | 3 Baths | -- Sqft
1695 Old Woods Path, Southold, NY 11971
House For Rent

available FALL '21 or in 2022: Southold, North Fork Estate Bayfront Rental... Private location but close to town... Direct bayfront residence with historic provenance. Broad porch, living room w/fp, formal dinning room, den, large kitchen and pantry...upstairs are five bedrooms. Direct on the beach setting - sugar sand and carefree days await. Pets considered - inquire.

$8,000/mo
5 Beds | 5 Baths | 3,500 Sqft
495 N Parish Drive, Southold, NY 11971
House For Rent

Southold, North Fork: Bayfront Bliss on the BEACH - all inclusive contemporary home vacation rental features 5 en suite master bedrooms and 5 full baths - NEW furnishings - immaculate! Pets considered. Weekly rate, two week min stay. Tenant pays exit cleaning.

$28,000/mo
4 Beds | 4 Baths | 3,200 Sqft
950 Blue Marlin Drive, Southold, NY 11971
House For Rent

Located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. It is truly stunning.

$45,000/mo
5 Beds | 5 Baths | 3,500 Sqft
920 E Cedar Point Drive, Southold, NY 11971
House For Rent

*** MEM -LABOR -RENTED! *** FLEXIBLE RENTAL, OFF SEASON, STILL AVAIL JAN -MEM DAY & OCT-DEC CALL/TEXT LAS FOR PRICING Spectacular waterfront Hamptons style home in Cedar Beach community w/private beach. Incredible unobstructed views of Peconic Bay from almost every room. Home sits on 1.4 private acres with amazing bluestone patio to watch the sunrises & sunsets. Tastefully decorated, perfect for entertaining! Open floor plan with EIK & dining area, 2 living rooms and cathedral ceiling great room w/FP. 5 Bedrooms including 2 ensuite. Master Bdrm w/WIC and Spa bath, French doors to private deck. 2 first floor bedrooms -1 ensuite. 2 Second floor bedrooms w/full bath. Winter, Spring, Summer or Fall- whatever season your prefer - this home is stunning and the views are amazing!

$25,000/mo
4 Beds | 5 Baths | -- Sqft
57305 Route 48, Greenport, NY 11971
House For Rent

Spectacular,contemporary home with Long island sound front .150 ft of direct waterfront and beach, with incredible views.Home situated one 1acre,6,600sq 2masters,1bedrooms(3king size bed)4,5 full baths,eat-in/kit.ld/dr,fr/lib.cant/air,2TV Wifi,jacuzzi &Steam Room.Outdoor sound system,and newish furnished.inground pool,outdoor shower room.all with direct water access.The best in coastal living.

$30,000/mo
3 Beds | 2 Baths | 2,000 Sqft
470 Goose Creek Lane, Southold, NY 11971
House For Rent

Dine Al Fresco And Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Masters Suite. New Soft padded Heated/Lighted IG Pool W/Automatic Cover, Unobstructed Waterviews & Enclosed Outdoor Shower. HI End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. All utilities included! Available For June 2021 & Then Again For September 2021thru June 2022

$3,000/mo
2 Beds | 1 Bath | 800 Sqft
430 Terry Lane, Southold, NY 11971
House For Rent

Picture Perfect 2-bed, 1-Ba Cottage in Founders Landing. 2 Pristine Beaches Nearby. Chic & Simple Beach House, Completely Renovated. Private Backyard. A Great Place From Which to Explore All the North Fork has to Offer.

$65,000/mo
4 Beds | 4 Baths | 2,400 Sqft
405 Cedar Point Drw, Southold, NY 11971
House For Rent

Impeccable home with numerous upgrades. Tastefully decorated. 4 Beds, 3.5 Baths with watervviews. New in-ground pool, Hot Tub. Private community bay beach. Ready For Summer Fun? Come To The North Fork... Everybody's Doing It!!

$57,500/mo
3 Beds | 3 Baths | -- Sqft
845 Budds Pond Road, Southold, NY 11971
House For Rent

Turn key bayfront home on a quiet cul-de-sac. This modern up-to-date home is a perfect year-round escape. Master suite plus 2 bedrooms, 2.5 baths. Plenty of room to work and play at home. The Outdoor Area Has A Deck For Enjoying The Waterfront Year-Round. Rented- Nov, - Feb 2021

$60,000/mo
3 Beds | 3 Baths | -- Sqft
200 Gin Lane, Southold, NY 11971
House For Rent

Brand new gunite pool with heater - ready for Spring use. Deeded beach. Modern, spacious - 3 bedrooms, 2.5 baths, open plan, fireplace. One bedroom with deck overlooking pool. Walk, bicycle, or drive to Cedar Beach, town, vineyards nature walks, and shopping. North Fork dream.

$85,000/mo
4 Beds | 4 Baths | 4,000 Sqft
1205 Lake Drive, Southold, NY 11971
House For Rent

Fabulous home on the Great Pond! Lakefront property with panoramic views of LI Sound. Large heated pool, 2 outdoor fire pits, seating for 10 or more & retractable awning. Master suite with fireplace and ultramodern fitness room with professional grade equipment. - 4 bedrooms (two on first floor), 4 baths & 3 fireplaces in all. Fully automated Alexa smart house. Work at home and be inspired!

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