Apartments for rent in Town of Southold NY

Rental Registration #: 2024-L-0047 LONGVIEW: This lovely, recently updated, beach house is ready for Summer 2024! Private and cozy. Near Shell Beach and Bootlegger's Alley. 3 bedrooms, 2 baths. Primary with ensuite., Outdoor patio, covered porch. Asking: June: $7K, July: $12K, August to LD: $14K, July 1 -LD: $24K, MD-LD: $27K. Other dates available. Please call for additional information

Did someone say private pool and tennis court? We did! This home is the perfect getaway for those looking to continue their active lifestyle all throughout their vacation. Circle drive features a private tennis court with a basketball hoop and a fenced-in private pool. Spend the afternoon grilling on the massive deck where guests can enjoy the summer sun. If that isn't enough, take a stroll down to the beach and enjoy the salty Peconic River.Please note: Additional date ranges available upon inquiry.

Rental Registration #: 2024-L-0028 This newly updated ranch house on Tuthill Drive (a private road on Big Ram Island) has been reimagined with the greatest attention to detail and quality. The open plan connects a spacious sun and (high fidelity) TV room with living room (and wet bar),cook's kitchen, and full dining room Three bedrooms include a private guest suite (with steam shower)primary and secondary bedrooms both ensuite,(the primary with a large double ended,clawfoot tub),all with radiant heated tile bathroom floors The sunroom and living room are separated by a modern wood fireplace opening to both rooms. Moroccan rugs , interesting art, and designer furniture pepper the house .The exterior property has a large, private, beautifully landscaped rear garden with a heated Gunite pool and bluestone patio seating and dining areas. At the rear of the property is a single car garage and private driveway connected to South Ram Island Drive,providing the property with access from two roads. A short half mile from the house is majestic Reel Point,a peninsula shaped beach that forms the entrance to Coecles Harbor. A little more than a half mile in the other direction is the historic Ram's Head Inn where one can end the day with sunset drinks and dinner.23 Tuthill is a wonderful summer get-away where one can relax, entertain, and enjoy the quiet and surrounding beauty.

Rental Registration #: Pending Shelter Island Heights Victorian residence, brilliantly restored and carefully expanded, offers classic details - extraordinary wide plank floors, elegant moldings, window and door trim, classic fireplaces and ornate doors. Double parlors, gorgeous eat-in-kitchen outfitted for easy entertaining leads to a spacious porch overlooking lush garden and heated gunite pool. The breath-taking wrap around porch at the front on the property offers endless reasons to entertain. The second floor consists of 4 bedrooms, including a spacious primary suite, and full bath. A large guest cottage is located at the rear of the garden. The cottage consists of two bedroooms, a full bath, a living room and kitchenette. Truly a dream house - restored and appointed with an artist's eye offering the best in taste, comfort and enjoyable living. The location cannot be beaten - minutes walk from the North Ferry, Shelter Island Yacht Club and all the heights has to offer.

Rental Registration #: Pending Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to immerse you in the beauty of the surrounding waters. Expansive waterfront decks filer out of every room. A guest bedroom and a full bath finish off the ground floor. The second floor consists of an oversized primary suite with private deck and breath-taking views of the bay. An additional guest suite and laundry room complete this floor. The outdoors also envelops you with luxury: a waterside heated infinity pool, multiple covered porches for dining or relaxing, dining pavilion, and built-in gas grill. The meticulously landscaped garden blooms all summer long, and features professional landscape lighting. You'll be enchanted by this garden's beauty day and night. Take full advantage of this magnificent waterfront property. Your oasis awaits.

Wake up smiling every morning in this sun-filled house. Spend days lounging and evenings grilling and dining around the 40' long pool. Relax inside on the comfortable museum quality modern furniture or warm yourself by the hanging, rotating fireplace.You can walk down the deeded right-of-way to a small, private beach on Coecles Harbor or you can bike (or drive 5 minutes) to larger beaches, to the markets and to town. The house is 3 minutes from the Mashomack Preserve, over 2000 acres of interlacing tidal creeks, mature oak woodland, fields and freshwater marshes. The Perlman Music Program and the Bay Street Theater are short drives away. Easily accessible from L.I., the house is 4 minutes from South Ferry and 7 minutes from North Ferry.The house is fully outfitted with internet, WiFi, linens, a fully furnished kitchen and washer/dryer. The kitchen is all stainless steel with a Sub-Zero refrigerator, Bertazzoni range, Blomberg dishwasher and GE microwave. The house has geothermal HVAC.Designed by it's owners, noted architects Paul Aferiat and Peter Stamberg of Stamberg Aferiat + Associates, the house has been published extensively in the US and abroad, as well as having been featured on several television shows. The house is in two parts. One consists of a living/dining room, kitchen, master bedroom and bathroom. The other consists of 2 bedrooms, a convertible TV room and 2 bathrooms. For the architecturally inclined, the house design is a reexamination of Mies van der Rohe's 1929 Barcelona Pavilion from a 21st Century perspective. For more information about the design, please visit stambergaferiat.com. In addition to the photographs and design statement, the website includes links to magazine articles and TV segments.*Pets are prohibited unless our express approval is givenPlease note: Additional date ranges available upon inquiry.

Rental Registration #: Pending Set minutes from Coecles Harbor, this magnificent 3 bedroom home has been newly renovated with designer finishes and can be yours for the summer and beyond! The light-filled great room overlooking the terrace which adjoins the brand new kitchen, where you'll find professional-grade appliances, stone countertops and ample storage.There's also a formal dining room and a den/media room. The luxurious primary suite has an abundance of natural light, tons of walk-in closet space, and a designer bathroom. All the guest room are very spacious, bright and tastefully furnished. You'll love the gorgeous gardens and outdoor living space. Minutes to the beaches and all the wonderful offerings of Shelter Island.

Dering Harbor Traditional Victorian residence, brilliantly restored and carefully expanded, offers classic details - extraordinary wide plank floors, elegant moldings, window and door trim and a classic fireplace. Double parlors, formal dining room, gorgeous eat-in-kitchen and prep kitchen outfitted for easy entertaining leads to a spacious screened porch overlooking lush garden and heated gunite pool. There are 5 bedrooms, including a luxurious master, 3 1/2 baths . Truly a dream house - restored and appointed with an artist's eye offering the best in taste, comfort = CAC and set in a romantic, private garden with inviting pool within the village. An expansive deep water dock supplements this extraordinary property - truly a boaters dream house.

Bright and open 4 bedroom 3 bath contemporary home with a spacious floor plan and plenty of exterior areas for lounging and barbecuing on the deck or by the heated pool. The partially finished basement and game room will be fun for the kids. Well equipped with central air, cable/internet, fireplace, garage, outdoor shower, hot tub & heated pool. July $25,000; August $27,000; August-LD $30,000.

Rental Registration #: 2023-l-0033 Shelter Island is nestled between the North and South Forks of eastern Long Island. This newly constructed 3-bedroom farmhouse, situated on a private .94 acre of property, is located just 2 minutes from the North Ferry making it easy to head over for a visit to the Seaport town of Greenport. In Greenport you will find plenty of shops, galleries and restaurants to enjoy. You can also take a wine tasting tour of the many vineyards along the North Fork. The home is located just one mile from beautiful sunsets at Crescent Beach which hosts Sunset Beach Restaurant. You can dine at Leon 1909, stop in at the Tuck Shop for Ice Cream, or play a round of golf at Shelter Island Country Club, all are within walking distance of the residence. There are so many lovely places on the Island to dine such as The Chequit, The Pridwin, The Rams Head Inn, Stars Cafe, Salt and the Eccentric Bagal just to name a few. All are just minutes away. If you like craft beer the Island has its own Shelter Island Brewery, or you can stop in at White Oak farm and enjoy some of the wines and cheeses that they offer. The South Ferry brings you into the Seaport town of Sag Harbor where you can find Bay Street Theater, Sag Harbor Cinema with its third-floor rooftop terrace bar "The Green Room", and tons of shops and dining experiences. Relaxation is plentiful while you enjoy life between the ferries at either one of the islands scenic beaches, hiking amongst nature in Mashomack Preserve or hanging around the house. The living Room is open to the kitchen allowing fireplace views from every angle of the main living area. The rear patio is equipped with a propane fire pit. The primary bedroom also has its own fireplace and boasts a large private bath with soaking tub and walk in shower. All bedrooms are suite style and are equipped with smart tv's. There is a large media room on the second floor, and you will find a billiard room at the lowest level that is equipped with a wet bar for entertaining. The garage has a small indoor basketball court for exercise on rainy days. The home is fitted with a Sonos system for music and has WIFI access points on each floor as well as outside. The home is ready to go for the summer season and can also be available for 15-day stays.

Rental Registration #: 1102 Rental Permit # 1102 Welcome to 1405 Terry Lane, Orient, a fully renovated waterfront residence with a private beach that extends for miles in each direction and a new, heated 20 x 40 in-ground pool with views overlooking the Long Island Sound. Situated on 1.63 acres at the end of a private road, a remote gated entrance opens to a white stone driveway that passes by a private half acre vineyard and consummates at the 3 bedrooms, 2.5 bathroom home with the master bedroom with en-suite bathroom on the first floor. The home has hardwood floors throughout, a modern kitchen with expansive views of the Long Island Sound, a four seasons room that lead to an spacious deck with awnings and all of the amenities one could ask for when entertaining guests. The sprawling lawns and have manicured landscaping and plantings private both room to play, privacy, incredible sunsets and a serene environment. This is truly both a remarkable and unique getaway to spend your summer months.

Rental Registration #: 0473 Come to the beautiful North Fork and spend your summer in this outstanding, stylish home in private sound front community at 560 Grandview Drive, Orient. Large bright home with 4 bedrooms and 3 baths, great room with fireplace, primary bedroom en-suite with fireplace, super floor plan and chic furnishings, set on 1 acre, heated pool with Jaccuzzi; ready for your off season or summer vacation and beyond. Close to beautiful beaches, Orient village, and the Jitney. Available June $14K, July $30K, August-LD $35K. Year Round $8,500/monthly. Rental Permit# 0473

Rental Registration #: 0625 Available for 2024! Newly constructed modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar. Past tenants all loved their stay at this home!!

Rental Registration #: 0863 Step into summer in Orient this year. Relax and rejuvenate in the quiet soundfront beach community of Orient by the Sea. Sunny open concept floor plan incudes glass doors that lead out to the covered backyard deck and invites indoor and outdoor entertaining. Just a short drive away to Greenport's many restaurants, the area's popular wineries for a tasting. Or enjoy a bike ride to Orient Beach State Park for a peaceful day on the bay. MD-LD $20,000 June $5,000, July $8,000 Aug $10,000 Permit #0863

Rental Registration #: 0812 Year Round ONLY $4500! This Perfect Get Away Home Consists Of 3 Large Bedrooms, 1.5 Bathrooms, A Spacious EIK, Bright Open-Plan Living Room, Laundry And Recently Installed In-Ground 20 x 40 Saltwater Swimming Pool! This Gem Of A Home Was Completely Renovated To A Premium Standard In 2021. It Is Fully Furnished And Contains All New Modern Appliances. Close To The Cross Sound Ferry, Orient State Park And Public Marina. Reserve A Viewing Right Away And Avoid Missing Out On This Beauty! May: $6,000 - June: $10,000 - July: $18,000 - August to LD: $18,000 - September: $9,000 & MD to LD: $32,000. Rental Permit #: 0812

Rental Registration #: 2024-L-0047 LONGVIEW: This lovely, recently updated, beach house is ready for Summer 2024! Private and cozy. Near Shell Beach and Bootlegger's Alley. 3 bedrooms, 2 baths. Primary with ensuite., Outdoor patio, covered porch. Asking: June: $7K, July: $12K, August to LD: $14K, July 1 -LD: $24K, MD-LD: $27K. Other dates available. Please call for additional information

Did someone say private pool and tennis court? We did! This home is the perfect getaway for those looking to continue their active lifestyle all throughout their vacation. Circle drive features a private tennis court with a basketball hoop and a fenced-in private pool. Spend the afternoon grilling on the massive deck where guests can enjoy the summer sun. If that isn't enough, take a stroll down to the beach and enjoy the salty Peconic River.Please note: Additional date ranges available upon inquiry.

Wake up smiling every morning in this sun-filled house. Spend days lounging and evenings grilling and dining around the 40' long pool. Relax inside on the comfortable museum quality modern furniture or warm yourself by the hanging, rotating fireplace.You can walk down the deeded right-of-way to a small, private beach on Coecles Harbor or you can bike (or drive 5 minutes) to larger beaches, to the markets and to town. The house is 3 minutes from the Mashomack Preserve, over 2000 acres of interlacing tidal creeks, mature oak woodland, fields and freshwater marshes. The Perlman Music Program and the Bay Street Theater are short drives away. Easily accessible from L.I., the house is 4 minutes from South Ferry and 7 minutes from North Ferry.The house is fully outfitted with internet, WiFi, linens, a fully furnished kitchen and washer/dryer. The kitchen is all stainless steel with a Sub-Zero refrigerator, Bertazzoni range, Blomberg dishwasher and GE microwave. The house has geothermal HVAC.Designed by it's owners, noted architects Paul Aferiat and Peter Stamberg of Stamberg Aferiat + Associates, the house has been published extensively in the US and abroad, as well as having been featured on several television shows. The house is in two parts. One consists of a living/dining room, kitchen, master bedroom and bathroom. The other consists of 2 bedrooms, a convertible TV room and 2 bathrooms. For the architecturally inclined, the house design is a reexamination of Mies van der Rohe's 1929 Barcelona Pavilion from a 21st Century perspective. For more information about the design, please visit stambergaferiat.com. In addition to the photographs and design statement, the website includes links to magazine articles and TV segments.*Pets are prohibited unless our express approval is givenPlease note: Additional date ranges available upon inquiry.

Rental Registration #: 2024-L-0028 This newly updated ranch house on Tuthill Drive (a private road on Big Ram Island) has been reimagined with the greatest attention to detail and quality. The open plan connects a spacious sun and (high fidelity) TV room with living room (and wet bar),cook's kitchen, and full dining room Three bedrooms include a private guest suite (with steam shower)primary and secondary bedrooms both ensuite,(the primary with a large double ended,clawfoot tub),all with radiant heated tile bathroom floors The sunroom and living room are separated by a modern wood fireplace opening to both rooms. Moroccan rugs , interesting art, and designer furniture pepper the house .The exterior property has a large, private, beautifully landscaped rear garden with a heated Gunite pool and bluestone patio seating and dining areas. At the rear of the property is a single car garage and private driveway connected to South Ram Island Drive,providing the property with access from two roads. A short half mile from the house is majestic Reel Point,a peninsula shaped beach that forms the entrance to Coecles Harbor. A little more than a half mile in the other direction is the historic Ram's Head Inn where one can end the day with sunset drinks and dinner.23 Tuthill is a wonderful summer get-away where one can relax, entertain, and enjoy the quiet and surrounding beauty.

Rental Registration #: Pending Shelter Island Heights Victorian residence, brilliantly restored and carefully expanded, offers classic details - extraordinary wide plank floors, elegant moldings, window and door trim, classic fireplaces and ornate doors. Double parlors, gorgeous eat-in-kitchen outfitted for easy entertaining leads to a spacious porch overlooking lush garden and heated gunite pool. The breath-taking wrap around porch at the front on the property offers endless reasons to entertain. The second floor consists of 4 bedrooms, including a spacious primary suite, and full bath. A large guest cottage is located at the rear of the garden. The cottage consists of two bedroooms, a full bath, a living room and kitchenette. Truly a dream house - restored and appointed with an artist's eye offering the best in taste, comfort and enjoyable living. The location cannot be beaten - minutes walk from the North Ferry, Shelter Island Yacht Club and all the heights has to offer.

Rental Registration #: 478 Lagoon Lodge is a charming waterfront home with 3 bedrooms, and 2 bathrooms, and has central air and high-speed internet! In the heart of the North Fork of Long Island, in the hamlet of East Marion, New York. The home comfortably sleeps up to 4 people. The property sits right on the water and steps to the beach.Upstairs is the bedroom with a queen bed. The main area upstairs has 2 twin beds that can sleep 2 guests. Downstairs is a queen bedroom with a king-size trundle. There are 2 full bathrooms plus an enclosed outside shower. The hallway linen closet has towels for the bath and beach, sheets, and other comforters.Enjoy sumptuous meals in the eat-in kitchen. The sliding glass doors off the kitchen lead to the open deck providing ample outdoor dining tables. If you are up to doing some grilling, the spacious yard with a gas grill is the perfect spot for you.There is a Lavender farm, and various other farm stands for the group to explore in the immediate area! Consider booking a lighthouse cruise to Long Beach Bar "Bug" Lighthouse, golf at Island's End golf course, and walk to Sep's farm stand for local produce, kayak, or paddle boards to put in on our private beach. Don't forget your fishing gear to fully immerse in the beach experience.Situated between Orient and Greenport, you can arrive by the New London Ferry into Orient, by Hampton Jitney into East Marion, by the LIRR into Greenport, or by car. The North Fork has over 40 wineries within 10 miles, a State Park in Orient, and an old shipping village in Greenport (frequently written about in the New York Times) with unique shops and waterfront dining. Take a visit to Shelter Island and Sag Harbor via ferry out of Greenport.Rental Permit#: 0478NEARBY ATTRACTIONS:As avid outdoor lovers, we highly recommend exploring the area! Below are a few of our favorite attractions and the distance from the property:- Lavender by the Bay (0.7 miles)- Arbor View House Bed and Breakfast (0.7 miles)- Skate Park (2.2 miles)- Truman Beach (2.4 miles)- 67 Steps Beach and Permit Parking (2.5 miles)If you are looking for multiple homes that are close by for additional family and/or friends please inquire! We have many other beach homes within close proximity.

Rental Registration #: 0038 Situated on the North Fork of Long Island in the hamlet of East Marion, New York. This charming Lavender Fields Retreat has 3 bedroom, 2-bath ranch-style cottage and is a 2-hour drive from NYC. The home sleeps up to 8 people and is approximately 1,200 square feet. The spacious yard backs up to the area lavender farm, Lavender by the Bay, and is a short walk to the Association beach.Into the cottage, you will walk into the cozy living room with a wood-burning fireplace. There are 2 rooms with a queen bed and the 3rd bedroom has a bunk bed with a trundle. The property also has 2 bathrooms plus an enclosed outside shower. The eat-in kitchen is fully equipped for the chef in the family. Washer and dryer are also available for guest use. Sliding glass doors off the kitchen lead to the open rear deck providing ample outdoor dining tables. You can also step into the covered front deck for additional seating. The spacious yard includes a gas grill, outdoor fire pit with seating and hammocks.Consider booking a lighthouse cruise to Long Beach Bar "Bug" Lighthouse, golf at Island's End golf course, walk to Sep's farmstand for local produce, rent kayaks or paddle boards to put in on our Association's Spring Pond or Gardiner's Bay. Don't forget your fishing gear to fully immerse in the beach experience.Situated between Orient and Greenport, you can arrive by the New London Ferry into Orient, by Hampton Jitney into East Marion, by the LIRR into Greenport, or by car. The North Fork has over 40 wineries within 10 miles, a State Park in Orient, and an old shipping village in Greenport (frequently written about in the New York Times) with unique shops and waterfront dining. Take a visit to Shelter Island and Sag Harbor via ferry out of Greenport.

Rental Registration #: 0368 Mid-Century Contemporary with views of Long Island Sound in a private community with association beach across the road. Cathedral ceilings & large windows add to the bright & open feeling of the communal area. Water view deck for relaxing and entertaining. 1000 sf of living area plus 800 sf walk-out basement converted to a fully renovated recreation room/office with recessed lighting, new furniture, renovated bathroom, and laundry. Offered June $8,000; July $11,000; Aug $13,000; MD-LD $30,000; year $4,000/mo. Permit# 0368

Rental Registration #: 1040 This beautifully furnished private deeded beach home is available to rent year-round or seasonal. The home is super clean and move in ready! There are three large bedrooms, three full bathrooms, a living room on each floor, updated kitchen, hardwood floors and central air conditioning. Amazing location just a few homes away from the sound beach to enjoy swimming, fishing and sunsets! Southold Town Rental Permit #1040

Rental Registration #: 546 Private, peaceful home on a serene acre of property with mature plantings and wonderful landscaped greenery. Just renovated, featuring open modern Kitchen/Dining combo for modern entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto expansive front yard. Back deck with grill overlooks pool and backyard. Three bedrooms: 1 Queen, 2 full beds and primary with king bed and en-suite bathroom with large shower. Hall bathroom with tub. Laundry in basement. Tasteful furnishings, all the basics & wifi together make this an easy place to settle in and retreat to for a great vacation & workplace away from the everyday home office. Treadmill for workouts. Beach rights at the end of Bay Avenue. The surrounding area has it all: vineyards, farm stands, restaurants, beaches, downtown Greenport and more. Avail for use: Fire Pit - Solo Stove, 3 bikes. No cats, Dogs okay. Summer 2023 is booked. Now taking reservations for early spring getaways and fall wine country escapes! Click on availability tab for more details.