Vacation Home Rentals By Owner In Southold, NY

Enjoy a relaxing North Fork getaway in this spacious vacation rental, ideally located just minutes from Southold Town Beach, acclaimed local wineries, and the vibrant village of Greenport—home to charming shops, top-rated restaurants, and a variety of family-friendly activities.This well-appointed home offers plenty of space for the whole family, featuring three en-suite bedrooms, plus an additional bedroom and full bath. The open-concept kitchen connects seamlessly to the dining and living areas, where a cozy fireplace adds comfort and character.Sliding glass doors lead to a deck overlooking a large backyard, ideal for outdoor dining or unwinding after a day of exploring. The two-car garage includes an overhead screen door, creating a casual indoor-outdoor lounge space for added enjoyment.Whether you’re relaxing on the beach, wine tasting, or exploring historic Greenport, this home is your perfect North Fork retreat.Please note: A strict 2-week minimum stay is required.

Spacious Vacation 4BR Home Near Southold Beach, Greenport, and Top Wineries

Southold, New York, United States

4

Bed

4

Bath

Sleeps

$1087.5

Available August - Labor Day 2021!! $30,000.00brbrTake a long walk on the beach or set sail in Southold Bay for Shelter Island it's all at your finger tips on this property. After a long day of play, imagine watching the sky turn bright orange in front of you as the sun dips into the horizon on your expansive deck while entertaining quests with appetizers and refreshing spirits.brIt can all happen here!brThis expansive floor plan (3,000 sq. ft. approx.) has three bedrooms (fourth optional) all with walk-in closets, the master bedroom located on the main floor has a king sized bed with attached bath and Jacuzzi. Upstairs there is a second living area, two bedrooms (recently replaced the twins) with queen sized beds and one bath. Both bathrooms have double sinks and there is a half bath for guests and one full bath located off the recreation room on the lower level. (3 levels)

One block from the beach!!

Southold, New York, United States

Bed

Bath

Sleeps

$775.29

Gorgeous, renovated 4 bedroom waterfront home in prime Southold. brEnjoy an outdoor fire next to the bay, or cozy up next to the wood burning fireplace indoors. Grill & dine outside or soak in the wood burning hot tub. Swim in the bay from your private low-tide beach, or walk steps to the community beach. When it’s time to play, borrow the kayaks and paddleboards, or play basketball, bocce or tetherball.brbrLocated within a mile of downtown Southold, and ~3 miles from Greenport. Close to fish market, farmstands, a marina & wineries.

Nautical Peconic Bayfront Home - Walk to Town

Southold, New York, United States

4

Bed

5

Bath

Sleeps

$965

Summary:brbrWaterfront home on Goose Creek with a private dock and kayaks for direct water access. Three bedrooms and three full baths. Designed for extended North Fork stays, minutes from beaches, vineyards, and farm stands.brbrbrbrThe Space:brbrThree-bedroom waterfront home on Goose Creek with a private dock, kayaks, and three full baths. Two-week minimum. Ideal for extended North Fork stays near vineyards, beaches, and farm stands.brbrbrbrThis waterfront home sits directly on Goose Creek in Southold, with a private dock, kayaks, and wide water views from the back deck. The property is on a quiet residential street and offers a comfortable layout for families or small groups booking two weeks or longer on the North Fork.brbrbrbrThe main level centers on an open living and dining area with a coffered vaulted ceiling, hardwood floors, and a wall of glass doors to the rear deck. A reclaimed wood dining table seats eight under a sputnik chandelier. The kitchen has Bosch wall oven and microwave, a gas cooktop on the island, black granite countertops, white shaker cabinetry, and pendant lights. The primary bedroom is on the main level with a king bed, vaulted ceiling, arched windows, and french doors to the yard with creek views. The ensuite bath has a double vanity, glass-enclosed shower, and stone tile floors.brbrbrbrTwo additional bedrooms are upstairs: one with a queen bed, skylight, and creek views through dormer windows, one configured with two twins, a toddler bed, and a crib. Three full bathrooms serve the home. A den off the kitchen has a built-in entertainment center, TV, workspace with dual monitors, and board games.brbrbrbrThe backyard opens to the creek and dock with direct water access for kayaking. A rear deck has a retractable awning, outdoor dining for six, and a gas grill. A fire pit and lawn seating face the water.brbrbrbrCedar Beach County Park is a 6-minute drive (2.5 miles). Goose Creek Beach is a 4-minute walk. Sparkling Pointe, Croteaux, The Old Field, and other North Fork vineyards are all within a 5 to 7 minute drive. Southold Village, farm stands, and local dining are nearby.brbrbrbrSeasonal Availability of Outdoor Amenities brbrOutdoor amenities, including kayaks, patio furniture, and grills, are typically stored between Columbus Day and Memorial Day. Contact us with questions about specific amenities during your stay dates.brbrbrbrWe manage several properties in the area. Contact us for group booking options.brbrbrbrRental Permit#: 298brbrbrbrIMPORTANT NOTES: brbr• The primary renter must be at least 25 years old. brbr• Pets may be permitted with prior approval and an additional pet deposit. brbr• For security purposes, this property has a Ring camera installed at the exterior entrance.brbr• For stays over 21 days, any extra utility costs beyond the initial charged amount are the guest's responsibility. brbr• For reservations of 29 nights or more, a refundable deposit will be collected prior to arrival. Our team will reach out for details upon booking.brbrbrbrGuest Access:brbrGuests have full private access to the home, yard, dock, and waterfront area.brbrbrbrThe Neighborhood:brbrNEARBY ATTRACTIONS:brbr• Goose Creek Beach: 4-minute walk (0.3 miles)brbr• Founders Landing Park: 10-minute walk (0.5 miles)brbr• Cedar Beach County Park: 6-minute drive (2.5 miles)brbr• Sparkling Pointe Vineyards & Winery: 5-minute drive (2.0 miles)brbr• Croteaux Vineyards: 4-minute drive (1.7 miles)brbr• The Old Field Vineyards: 4-minute drive (1.8 miles)brbr• Lavender by the Bay: 19-minute drive (9.5 miles)brbrbrbrGetting Around:brbrA car is recommended to explore the North Fork. Vineyards, farm stands, beaches, and Southold Village are all within a short drive.brbrbrbrOther Things to Note:brbrCancellation PolicybrbrBookings canceled at least 30 days before the start of the stay receive a 100% refund.brbrBookings canceled at least 14 days before the start of the stay receive a 50% refund.brbrbrbrGuest InsurancebrbrGuests are required to sign a Rental Agreement and are covered by a property damage protection policy. This policy covers incidental damage to the home during the stay and does not cover trip cancellation. Stays of 29 nights or more require a refundable security deposit.brbrbrbrWaterfront AdvisorybrbrThe property sits on Goose Creek. There are shallow areas and a low-clearance bridge at Bayview Road. Guests bringing watercraft should familiarize themselves with local conditions before launching. The property owner and management do not provide navigational guidance.brbrbrbrOur CompanybrbrLuxury Beach Getaway has offered curated vacation home rentals in the Hamptons and North Fork since 2008.brbrbrbrInteraction with Guests:brbrOur team is available by phone, text, or email throughout your stay.

Southold Waterfront Home on Goose Creek | Dock, Kayaks, Creek Views

Southold, New York, United States

Bed

Bath

Sleeps

$971.15

Please note that a reservation for this property needs to be approved before it is confirmed.brbrVilla Vino ModernbrbrNewly Constructed Modern Vacation Villa Minutes to some of the best wineries on the North Fork, Perfect for Familiesbrbr4BR/3BA: private pool, fire pit, BBQ, wifi, multiple sitting areas, modern and spacious, washer/dryer, island kitchen, open layoutbrbrSet in the tranquil heart of Southold, this stunning 4-bedroom, 3-bathroom vacation home promises a luxurious retreat on the North Fork. Nestled amidst the region's renowned wine country, it's a stone's throw away from Horton Point Beach and the exquisite Duck Walk Vineyards. Newly constructed, this home combines spaciousness with intimate charm, offering various sitting and dining areas that cater perfectly to family gatherings. Here, on a serene private block, escape the everyday to bask in a residence that has been expertly designed with you in mind. And for those sunny days Dive into the shimmering waters of your private pool, the epitome of vacation luxury.brbrBeyond the walls of this elegant home lies an oasis of exterior amenities. Enjoy total privacy, a rarity that ensures uninterrupted relaxation. The expansive patio, designed for both relaxation and entertainment, features comfortable sitting areas. Picture early morning breakfasts or late afternoon cocktails as you lounge by your pristine private pool. As dusk approaches, light up the BBQ for an alfresco feast and later, gather around the fire pit, where stories are shared, and memories are made. And for those arriving by car, the property offers ample free parking spaces, making your stay as convenient as it is comfortable.brbrStepping inside, guests are welcomed by an open layout awash with abundant natural light, creating an atmosphere of warmth and relaxation. Modern comforts, including high-speed WiFi, a washer and dryer, and central AC, are discreetly integrated, ensuring a seamless stay. The interconnected living spaces promise effortless flow, moving from the living room to the dining area and onto a gourmet island kitchen. Here, culinary enthusiasts can revel in top-of-the-line appliances. The formal living room, complete with a crackling fireplace and a TV, beckons for cozy evenings. Adjacently, a separate den, equipped with an additional media area, offers yet another haven for relaxation and entertainment.brbrEach bedroom in this resplendent retreat has been curated for unparalleled comfort and rest. Fresh, premium linens promise peaceful slumbers, while the bathrooms, stocked with essential amenities, assure that every guest feels pampered. Families are especially catered for with a dedicated kids room featuring fun bunk beds. Luxury takes center stage with two primary suites, each boasting ensuite bathrooms, providing a private sanctuary for relaxation after a day of exploration.brbrWhile the home stands as a beacon of luxury and relaxation, its coveted location adds layers to the vacation experience. A short journey will take guests to some of North Fork's most acclaimed wineriesDuck Walk Vineyards, Lenz Winery, and Bedell Cellars, to name a few. Just minutes from the front door guests will find pristine Kenney's Beach to the East, and Goldsmith's Inlet to the West. The nearby Horton Point Lighthouse Nautical Museum offers a dose of history, while its adjoining beach is a haven for sun and surf enthusiasts.brbrThis property has a max occupancy of 8brbrBedroomsbrbrBedroom 1: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Standard ClosetbrbrBedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, ClosetbrbrBedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, ClosetbrbrBedroom 4: One Twin Single Bed, One Double/Full Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBathroomsbrbrHallway Bathroom 1: Full Bath, 2nd Floor, Handicap Accessible, Shower/Tub CombobrbrPrimary Ensuite Bathroom 2: Full Bath, 2nd Floor, Ensuite, ShowerbrbrEnsuite Bathroom 3: Full Bath, 2nd Floor, Ensuite, ShowerbrbrHallway Bathroom 4: Full Bath, First Floor/Main FloorbrbrOutdoors & Pool/SpasbrLounge Chairs (2 Chairs), Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Deck/Patio (Uncovered), Grill (Gas), Private Pool (Outdoor, Heated)brbrAmenitiesbrBed Linens, Usable Fireplace (Gas-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Garage, Living Room, Parking, Bath Towels, Microwave, Coffee (Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Television (Main Living Room, Den), Kitchen, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Ice Maker, Laptop-Friendly WorkspacebrbrLocationbrbrNearby Beaches:brKenney's BeachbrGoldsmith's Inlet ParkbrHorton Lane BeachbrbrNearby Grocery Stores:brSouthold IGAbrWayside MarketbrbrNearby Restaurants and Bars:brBedell CellarsbrPindar VineyardsbrDuck Walk VineyardsbrNorth Fork Table & InnbrLa CascadabrbrOther Location Information:brFounders Landing ParkbrHorton Point Lighthouse Nautical MuseumbrbrOther FAQ'sbrbrBackyard Fenced In: YesbrbrSuitability: Primary renter must be at least 28 years old.brbrPet Policy: Pets are strictly prohibited at this property.brbrUtility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation.brbrCleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense.brbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement.brbrThe guest experience for this property is managed by StayMarquis, a local vacation rental management company. By booking this property, you will receive a dedicated Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Newly Constructed Modern Vacation Villa Minutes to some of the best...

Southold, New York, United States

Bed

Bath

Sleeps

$596.14

Baydreams is an amazing bayfront home ready for rent to create memories! Walk out onto the large deck which extends to the back lawn and down to the private beach where you can enjoy the calm bay with picturesque views of Shelter Island. Perfect to share with another family.

Waterfront home with private beach amazing view and sleeps 10 !

Southold, New York, United States

Bed

Bath

Sleeps

$1105.04

Just steps from a private sandy beach with a beautiful view across the Peconic Bay to Sag Harbor and perfect sunsets. House is equipped with beach chairs, umbrellas, beach games, kayaks, paddleboard, and rafts. Everything you need for a perfect day at the beach!brbrAfter the beach, take a soak and relax in a six-person hot tub and enjoy a hot shower outside under the stars, while the kids have fun in the basement game room with a 75'' screen TV, Xbox, Foosball, Ping Pong, Darts, and Golden Tee-Bowling Arcade Machine.brbrHave a BBQ on our home's huge back deck with a 9’ fire pit table and outdoor seating while viewing the scenic pond with daily visits from a family of swans.brbrThis fully renovated 4-bedroom ranch offers everything you need to enjoy the perfect vacation. We are centrally located to all the best Vineyards, Breweries, Downtown Greenport and all the best restaurants North Folk has to offer! Permit # 630

Water View Beach House just steps to Private Sandy Beach!

Southold, New York, United States

Bed

Bath

Sleeps

$1430.29

The Waterside HideawaybrbrModern Waterfront Southold Escape, Private Heated Saltwater Pool, Great for Friends and Familiesbrbr3BR/3BA: Waterfront, Heated Saltwater Pool, Gas Grill, Laptop-Friendly Workspace, Gas Fire Pit, Private DockbrbrNestled along the serene waterfront of Southold, this modern retreat offers a perfect blend of relaxation, luxury, and coastal charm. Designed with an open floorplan, this home provides an ideal setting for families, friends, or small groups seeking a memorable getaway. From the moment you arrive, youll feel the stress of daily life melt away as you step into a space that balances comfort and elegance, complete with seamless indoor-outdoor living. Light-filled rooms, tasteful dcor, and thoughtful design details create an inviting atmosphere where guests can unwind, gather, and reconnect.brbrThe exterior of the home is nothing short of spectacular. A private heated saltwater pool beckons for leisurely swims on warm afternoons, while the surrounding deck and lounge areas offer plenty of space to relax and enjoy the waterfront views. The gas fire pit creates a cozy ambiance for evenings spent under the stars, perfect for storytelling or enjoying a quiet night with loved ones. A gas grill allows for effortless outdoor dining, and the lush landscaping ensures total privacy, giving you the feeling of a secluded sanctuary just steps from the water.brbrInside, the homes open layout is ideal for both entertaining and quiet moments. The living spaces flow naturally from the living room to the dining area and into a fully equipped, modern kitchen featuring top-of-the-line appliances and a coffee maker for leisurely mornings. Large windows flood the interior with natural light, highlighting the contemporary finishes and thoughtfully arranged furnishings. Central air conditioning keeps the home comfortable year-round, and high-speed WiFi allows guests to stay connected or work remotely if desired. A washer and dryer provide added convenience, making longer stays easy and enjoyable.brbrThe three bedrooms are designed as restful retreats, offering fresh linens, ample storage, and cozy furnishings to ensure a good nights sleep. The bathrooms are stylish and well-appointed, stocked with all the essentials for a hassle-free stay. Each space has been carefully considered to provide both comfort and functionality, allowing guests to focus on making memories rather than worrying about the details.brbrBeyond the home, guests are just minutes from Southolds charming shops, restaurants, art galleries, golf courses, and beautiful beaches. The property is also just a five-mile drive to Greenport Village, offering easy access to its vibrant waterfront, boutique shopping, and renowned dining scene. Whether you choose to explore the local culture, enjoy a day on the water, or simply savor the tranquility of the property itself, this waterfront Southold escape provides a sophisticated yet relaxed base for an unforgettable experience. Every element of the home has been curated to combine modern luxury with coastal charm, ensuring your stay is both comfortable and memorable.brbrThis property has a max occupancy of 6brbrBedroomsbrbrPrimary Suite: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite BathroombrbrBedroom 2: One Queen Bed, First Floor/Main Floor, Air ConditioningbrbrBedroom 3: One Queen Bed, Lower Level, Air ConditioningbrbrBathroomsbrbrPrimary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, ShowerbrbrBathroom 2: Full Bath, First Floor/Main Floor, Jack & Jill, ShowerbrbrBathroom 3: Full Bath, Lower Level, ShowerbrbrOutdoors & Pool/SpasbrDeck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Gas), Waterfront, Private Pool (Outdoor, Heated, Saltwater)brbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee, Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television, Private Entrance, Parking, Smoke Detector, EssentialsbrbrLocationbrbrNearby Beaches:brGoose Creek Beach (3-min walk)brbrNearby Grocery Stores:brSouthold IGAbrWayside MarketbrbrNearby Restaurants and Bars:brRestaurants to add:brMaronisbrMichael AngelosbrFounders TavernbrSouthold Fish MarketbrSouthold SocialbrbrOther Location Information:brBedell CellarsbrPindar VineyardsbrDuck Walk VineyardsbrNorth Fork Table & InnbrLa CroteauxbrGreenport BrewerybrFounders Landing ParkbrHorton Point Lighthouse Nautical MuseumbrbrSuitability: Not handicap accessible.brPrimary renter must be at least 30 years old.brbrPet Policy: One dog of 30 lbs or less is permitted for an additional $500.00 per booking. Dogs over 30 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).brbrUtility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation.brbrCleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.brbrAdditional Guests: Additional guests are prohibited unless express approval is provided.brbrEvents Policy: Events are prohibited unless express approval is provided.brbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Modern Waterfront Southold Escape, Private Heated Saltwater Pool, Great for...

Southold, New York, United States

Bed

Bath

Sleeps

$737.16

Lovingly restored with new kitchen, refinished hardwood floors throughout, two full modern bathrooms, open fireplace, central air conditioning, cable TV, Wi F and washer dryer this home supplies all the amenities needed to enjoy a relaxing and comfortable family vacation. The 3 bedrooms each have a Queen bed, and the two full bathrooms are newly renovated. In addition there is a pull out sofa in the living room, outdoor shower and dining plus barbecuebrbrManaged by the Shorecrest Bed and Breakfast and Property Management , you can expect the cleanliness and level of Service a top rated BnB would provide to their guests. In addition renters of this property have access to the Long Island Sound beach via a private path, part of the Shorecrest Bed and Breakfast property close by.brWelcome to your waterfront retreat in Southold, NY! This charming single-story house, originally built in the 1920s, has been fully renovated to blend vintage charm with modern comfort. Featuring 3 spacious bedrooms and 2 full bathrooms, this property is perfect for families or groups seeking a memorable getaway.brbrNestled on the shores of Hashamomuck Pond, an inlet of Shelter Bay, the lush lawns lead to steps that descend to a small sandy beach, ideal for sunbathing or enjoying water activities. Inside, you’ll find a fully stocked kitchen, Wi-Fi, Smart TV, air conditioning, and on-site laundry, ensuring a comfortable stay. The open living spaces are filled with natural light, inviting you to relax after a day of exploration.brbrLocated near Long Island Sound Beach on the picturesque North Fork, this area is known for its fantastic restaurants, beautiful beaches, wineries, and farms, offering a true taste of the region. For dog lovers, we happily welcome your furry friends, so you can share this wonderful experience together.brbrThis property beautifully marries historical elements with contemporary design, showcasing original hardwood floors and thoughtfully restored fixtures that reflect the character of the era. Whether you seek a peaceful retreat or an adventure-filled vacation, this waterfront home is the ultimate destination. Book your stay today and create lasting memories in Southold!

Shelter Bay Cove - North Fork Waterfront with Private Dock & Bay Views

Southold, New York, United States

Bed

Bath

Sleeps

$538.61

This house is newly updated, beautifully furnished and comfortable. It is light and spacious with hard wood floors throughout. The house is a 3 bedroom, 2 bath home. The kitchen is fully equipped. The backyard has a spacious deck with seating, grill and barbecue pit for some summer fun. The home is located in the heart of Southhold near beaches, wineries, and a short drive to the village of Greenport. brMinimum two week stay required by the Southold Township.

Charming Northfork home.

Southold, New York, United States

Bed

Bath

Sleeps

$1199.63

Enjoy the beauty of Long Island's North Fork right here at our vacation house in Southold. Enjoy fabulous water views, boating, beautiful beaches, hiking, bicycling, discover wine country and so much more! Summer stays go from Sunday to Sunday or you can visit on weekends all other times of the year.brOur waterfront vacation home has a beautifully situated outdoor hot tub (on year-round), a large deck overlooking the water, a large flat yard, a waterside fire pit/patio with firewood provided, an outdoor shower, a park style charcoal grill, a gas grill and a quiet front porch for relaxing. Inside there are 3 full baths (a Jacuzzi in one of them), 4 large bedrooms, a fully stocked and beautiful kitchen and an open floor plan, WiFi, central air conditioning and a gas fireplace. The upstairs master bedroom has an outdoor veranda which overlooks the water. There’s plenty of room! brYou can hang out on the deck and have a family BBQ. Play yard games or go for a ride on your boat right from the floating dock. If you bring your boats or watercrafts you can use the boat ramp that is right in the back yard. Feel free to use our kayaks, canoes, stand up paddle board or paddle boat. brThe house is also located on a private gravel road with literally no traffic. You can rest assured that you and your children can safely walk to the beautiful bathing beach which is a short block away. Not only can you relax while watching the boats going by, but you will also find the most amazing shells of all kinds. Your kids can safely play and explore the beauty of all Southold has to offer! brbrTown of Southold Rental Permit # 0591brCounty of Suffolk Hotel Motel Tax ID: HMT23-10061brbrKeywords: House Waterfont Beach Boat ramp

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Southold, New York, United States

Bed

Bath

Sleeps

$2113.62

Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater pool, cozy fire pit, BBQ area, and ample outdoor seating. Ideal for family getaways or group retreats, the house is just minutes from renowned wineries, beaches, and charming local farm stands. With bright and spacious living areas, this home offers a perfect blend of comfort. Whether lounging by the pool or exploring wine country, experience the ultimate North Fork retreat!

Spacious Home with Pool in Southold

Southold, New York, United States

Bed

Bath

Sleeps

$1241.78

Our newly renovated Farmhouse is centrally located in Southold with easy access by bus, train or car. Enjoy your morning coffee as the sun rises over the farmfield. Spend an afternoon exploring the beauty of the North Fork, soak in the sun at one of the beautiful Peconic Bay or Long Island Sound beaches, enjoy live music at numerous wineries and/or breweries, browse unique local finds at one of many antique and/or quaint shops, and don't forget to stop by the bountiful farm stands. Cool off with a dip in the heated saltwater pool, enjoy dinner under the stars and reminisce around the fire pit.

Renovated American Farmhouse in the heart of Southold with heated saltwater pool

Southold, New York, United States

Bed

Bath

Sleeps

$597.05

Steps from Peconic Bay and Cedar beach. brbrStay in our Southold home in the heart of North Fork and enjoy the best the North Fork has to offer! The location is ideal with Cedar beach/Peconic Bay just a block away and all the beach essentials, kayaks included, with your stay. brbrOur 3 bedroom, 1.5 bathroom home is surrounded by award winning vineyards & farm stands. Southold town center is an 8min ride where you'll find restaurants, local shops, and a grocery store. For more restaurants, shopping or the ferry to Shelter Island/ South Fork, Greenport village is just a 12min drive away.brbrWe have 2 single kayaks (with wheels) for use. You can launch directly into the Peconic Bay off of Cedar Beach, (short walk from the house). There are also beach chairs, beach towels, and a folding wagon to carry equipment to the beach. brbrSleeps 6 people comfortably. 2 bedrooms with 1 queen bed in each and a 3rd bedroom with two twin beds. If you have 7 people, there is also a pull out queen sofa for use with sheets and pillows in the living room. If you have a little one, we have a crib with sheets and a highchair available for use as well. Additionally there is one full bath, one half bath and a enclosed outdoor shower. There are window A/Cs in the dining room, master bedroom, and guest room. The children's room has a ceiling fan and a floor fan.brbrHouse is fully equipped. Includes washer/dryer, fully stocked kitchen, sheets, towels, shampoo, soap etc. It has Wi-Fi and even a desk with a high definition monitor if you need a place to work. There is also YouTube TV (40+) channels. As mentioned, beach equipment is included (towels, beach umbrella, chairs, etc). There is also a record player and selection of records for your use. brbrThere is a bright & beautiful dining area with a door that leads to an outdoor patio. The patio has a full sized table and 6 chairs in case you prefer to eat in the fresh air. There are folding chairs for extra guests. There is a grill & fire pit for use as well. brbrTake a glass of wine out to the back yard or a cup of coffee down to the water to overlook the sound. Use the grill to cook up fresh fish from Southold Fish Market or just sit by the fire-pit to chat with friends & family. We also have a handful of yard games for your enjoyment!brbrWe look forward to hosting you and your family for a well deserved relaxing & fun vacation on the Fork! brbr** indoor fireplace is not in working orderbr

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold, New York, United States

Bed

Bath

Sleeps

$642.68

A stones throw to your private creek entrance or an 8 minute walk down a private road to the exceptional Goose Creek Beach. A quick bike ride to all the best wineries The North Fork has to offer, or to the quaint town of Southold with its wonderful restaurants/bars. Whatever you’re looking for, you’ll find yourself immersed in relaxation and North Fork living at this exceptional home that is fully renovated for the best quality of time spent together.

NorthFork Serenity, next to beach and wineries

Southold, New York, United States

Bed

2

Bath

Sleeps

$2060.61

Summary:brbrOne of the North Fork's rare bayfront retreats — private sandy beach, panoramic sunsets over the Peconic, and a heated waterfront pool define this modern, design-forward haven for guests who seek serenity and space.brbr• Private waterfront setting with direct sandy beach accessbrbr• Heated pool steps from the shorelinebrbr• Unobstructed westward sunset views across Peconic BaybrbrbrbrThe Space:brbrThis home is ideal for weekly and longer stays, offering a private sandy beach, a heated waterfront pool, and a quiet bayfront setting designed for guests looking to truly settle in.brbrbrbrSet directly on the Peconic Bay, this modern waterfront home offers a rare combination: private sandy beach access, uninterrupted sunset views, and a heated pool overlooking the water — a true North Fork escape for guests seeking space, privacy, and simplicity.brbrbrbrThe home sits steps from the shoreline, where guests move seamlessly from pool deck to beach throughout the day. Mornings begin with coffee overlooking the bay. Afternoons unfold on the sand or by the pool. Evenings end with sunsets stretching west across the water — visible from the deck, living areas, and primary bedroom alike.brbrbrbrInside, a bright open-plan layout features walls of windows that frame the water and bring the outdoors in. The living and dining areas are designed for relaxed gathering; the modern kitchen is fully equipped for easy meals at home. Four bedrooms — each with a queen bed — allow families or small groups to spread out comfortably. A sleeper sofa accommodates a ninth guest.brbrbrbrOutdoor living is central to the experience. The expansive deck includes a heated pool, lounge and dining areas, a fire pit, and direct access to the beach below — ideal for families, couples, or multigenerational groups who want a quiet, private waterfront setting without crowds or traffic.brbrbrbrBest suited for: Guests who value privacy over scene, waterfront access over proximity to nightlife, and a calm, design-forward home base for exploring the North Fork's beaches, vineyards, and farm stands.brbrbrbrThis is not a party house. It's a refined, peaceful retreat designed for guests who want their vacation to feel effortless, private, and genuinely memorable.brbrbrbrHighlights (deduplicated, reordered by impact)brbrbrbr• Direct bayfront location on the Peconicbrbr• Private sandy beach access — no permits, no crowdsbrbr• Heated pool overlooking the waterbrbr• Westward sunset views from deck, living room, and primary suitebrbr• Modern open-plan interior with floor-to-ceiling windowsbrbr• Fire pit for evening gatheringsbrbr• A quieter, more refined alternative to the HamptonsbrbrbrbrThis home is newer to the rental market, which is why you won't yet see guest reviews. Our team has managed waterfront properties across the North Fork and Hamptons since 2008, and we're available throughout your stay to ensure a seamless experience.brbrbrbrSeasonal Availability of Outdoor AmenitiesbrbrPlease note that all outdoor amenities, including pool, patio furniture, grills, and other exterior equipment, are typically stored away between Columbus Day and Memorial Day. If you have specific questions regarding these amenities, feel free to reach out to us for more information.brbrbrbrDue to the climate of the Northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. Seasonal Availability of Outdoor Amenities. brbrbrbrIf 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.brbrbrbrIMPORTANT NOTE:brbr- The primary renter must be at least 25 years old.brbr- The property has outdoor security cameras for safety and added peace of mind.brbr- There is a standard pet fee of $200 per pet, per stay. An additional $100 may apply for dogs that shed excessively.brbr- Properties with a heated pool incur a daily pool heat fee of $45. brbr- For stays over 21 days, please note that any extra utility costs beyond the initial charged amount are the guest's responsibility.brbr- For reservations of 29 nights or more, a refundable deposit will be collected prior to arrival. Our Team will reach out for further details upon booking.brbrbrbrThe Neighborhood:brbrNEARBY ATTRACTIONS:brbrAs avid outdoor lovers, we highly recommend exploring the area! Below are a few of our favorite attractions and the distance from the property:brbr- The Barn of Wading River (1.1 miles)brbr- Bakewicz Farms (2.3 miles)brbr- The Shoppes at East Wind (3 miles)brbr- East Wind Day Spa (3.2 miles)brbr- Wildwood State Park (3.4 miles)brbrbrbrOther Things to Note:brbrCancellation Policybrbr- Bookings canceled at least 30 days before the start of stay will receive 100%.brbr- Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrbrbrGuest InsurancebrbrPlease note, as a part of booking we secure insurance for your stay and will require you to sign a Guest Rental Agreement. This insurance is meant to cover any incidental damages to the property that may occur during your stay and does not cover any issues with your trip related to cancellation due to illness or other reasons. We understand that things happen by mistake or accident from time to time, we ask that you let us know when it happens. You’re covered with us - we’re invested in you having a worry-free stay!brbrbrbrOur CompanybrbrLuxury Beach Getaway has been proudly offering a curated selection of vacation home rentals in the Hamptons and North Shore since 2008, and we look forward to hosting your wonderful stay.brbrThank You, Debbie & Scott

Modern North Fork Retreat: Beachfront, Heated Pool

Southold, New York, United States

Bed

Bath

Sleeps

$490.56

Escape to our charming 3-bedroom vacation home in the heart of Southold, where you can immerse yourself in the beauty of the North Fork region. Nestled just minutes away from renowned wineries like Croteaux Vineyard, Raphael Winery, Pindar Vineyards, and Kontokosta Winery, this property offers the perfect blend of relaxation and exploration.brbrAs you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the essential appliances and utensils you need to whip up delectable meals. Unwind in the cozy living room, where a crackling fireplace and a smart TV with satellite/cable channels await. Enjoy the convenience of a washing machine and dryer, ensuring you can pack light and stay refreshed throughout your stay.brbrVenture outdoors and bask in the tranquility of the property's porch, fire pit, and beach loungers. Soak up the sun, dine alfresco, or gather around the fire pit for s'mores and stargazing. For those seeking a bit of entertainment, you'll find a selection of games and books to keep you and your loved ones engaged.brbrWhether you're seeking a peaceful retreat or a hub for your North Fork adventures, this vacation home offers the perfect setting. Immerse yourself in the region's renowned wineries, explore the charming local shops and restaurants, or simply relax and unwind in the comfort of your home away from home.

Between the Vineyard and Sea. Walk to sandy beach from this charming cottage.

Southold, New York, United States

Bed

Bath

Sleeps

$301.59

Minnehaha MarvelbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis prime property with water views and surrounded by lush greenery can be your perfect place to escape reality with your loved ones. Vacation here on gorgeous Long Island, where many festivals, events, markets, shops, and local eateries abound. Take the kayaks out for a spin on the creeks and rivers, or head to the beach to participate in fun rentals and excursions like paddleboarding, surfing, boating, parasailing, and every other waterfront activity imaginable.brbrUpon entry, you'll be met with a bright interior and a warm feeling of welcome throughout the space. Make yourself at home by sitting on the plush furniture, curling up by the fireplace with a good book, or carrying on a conversation with loved ones. Stream a movie marathon on the large TV in the living area while the chef of the group cooks up a storm in the kitchen, equipped with stainless steel appliances, a breakfast bar, and a formal dining table. The main suite is comfortable, with plenty of room to get a great night's rest from the day's activities. It boasts a TV for private viewing, a spacious closet, and a lovely en suite bathroom with a walk-in shower. Enjoy grilling barbecue and dining alfresco on the back patio, witnessing spectacular sunsets along the bay.brbrTHINGS TO KNOWbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: No parking available.brbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok

Southold, New York, United States

Bed

Bath

Sleeps

$898.35

Enjoy this comfortable farmhouse with seven bedrooms, living room, full formal dinning room for 10, eat in kitchen, wrap around porch and large backyard with fire pit and grill. Two blocks walk to a beautiful beach with fantastic sunsets. Surrounded by the lovely North Fork Wineries and Breweries and minutes away from Greenport Village marina, boutiques and restaurants.brRentals are a 14 night minimum per Town Of Southold Code. Message me for inquiries.

North Fork 7 Bedroom Farmhouse Escape

Southold, New York, United States

7

Bed