Vacation Home Rentals By Owner In Southold, NY

$386.5

Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay

Southold, New York, United States

Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern conveniences. Walk to town and walk to Peconic Bay. House features a charming outdoor shower, patio, deck and screened-in porch. Two bedrooms and full bath are located downstairs with two bedrooms and half bath upstairs. Central air conditioning and washer/dryer. Decorated lovingly -- one might call it charming chic. The kitchen is new with hardwood floors and French country table for dining inside vs. on the deck outside. Mature landscaping with arborvitaes providing lots of privacy on the property. The Founder's Landing Beach is a half mile away is great for children as it has a lifeguard as well as swing set, slide and merry-go-round plus a grassy area with picnic benches. Heaven on earth.

Bed

Bath

Sleeps

$771.19

/ Nightly

Private Vacation Home

Southold Soundfront Private Beach

Southold, New York, United States

Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a quiet place, this is for YOU.brThis is NOT a bluff beach. Walk right out the FRONT sliding door and you are ON the beach. Walk out the SIDE sliding door you are on the wrap around deck, with patio set barbecue grill, lounge chairs, and views in every direction. You can walk in either direction ON the beach for miles. Crystal sand, rocks, beach glass and glistening water around you. Public beaches require town parking permits which can quickly increase the cost of your stay at other non-beach front properties, but you don't need a permit since this is a private beach (no crowds, no restrictions). br57035brbrOne Bedroom has a full size bed, the other bedroom has twin bunk beds. Wrap around deck, with furniture on BOTH sides of house for morning and afternoon sun + beach chairs included. This house does have heat for cooler nights in Spring & Fall. Perfect for a long relaxing Summer, weekend get away, or family retreat. Really great fall fishing weekends, winery trips, pumpkin picking. Give us a call, you're going to LOVE IT !brbrAll rates listed are for a family of 4 (2 adult, 2 children). There are additional charges for extra guests and these need to be confirmed and agreed upon at time of reservation. Please note that we are vigilant about the number of people renting the house. Sorry, not pets allowed due to guests with allergies. brbrKeywords: Housebr

2

Bed

1

Bath

4

Sleeps

$1087.14

/ Nightly

Private Vacation Home

Waterfront North Fork Retreat • Sunsets, Beaches & Vineyards

Southold, New York, United States

Newly renovated waterfront getaway on the North Fork - 4BR/3BA, sleeps 8. Chef’s kitchen with premium appliances, Sonos speakers throughout, sun room, rec room, and a waterside patio with sunsets that stop you mid-sentence. Minutes from Greenport Village, Southold farm stands, and vineyards. Dedicated workspace, fast WiFi, laundry, AC, and driveway parking. Every room updated with modern finishes and the warmth that makes the North Fork special.brbrThe NYC getaway that you've been waiting for.

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Bath

Sleeps

$2521.23

/ Nightly

Private Vacation Home

Luxury North Fork Estate w/ Heated Pool & Walk to Southold Beaches

Southold, New York, United States

Luxury North Fork estate in Southold with a private heated saltwater pool, spa, and walk-to-beach access. Set on over an acre of landscaped grounds, this refined retreat offers indoor-outdoor living, total privacy, and easy access to Kenney’s and McCabe’s beaches—perfect for relaxed North Fork summers with family or friends.brbrOutdoor Living & Pool Experience:brThe outdoor spaces are the heart of this estate and are designed for effortless summer living. The expansive, private yard features a heated saltwater gunite pool and spa with a built-in safety cover, surrounded by mature landscaping for privacy. Enjoy al fresco meals on the main dining deck, evenings by the gas fire pit, and refreshing rinses in the private outdoor shower after beach days. Multiple seating and lounging areas make it easy for everyone to spread out and relax.brbrSleeping Arrangements & Comfort:brThe home is thoughtfully designed to accommodate families and multi-generational groups while maintaining comfort and privacy throughout. The ground-floor primary suite features French doors opening directly to the pool and gardens, along with a spa-like bathroom that includes a jacuzzi tub and walk-in shower. Two additional en-suite bedrooms are located in the main house. A private guest suite in the west wing is ideal for grandparents, another family, or a live-in nanny and includes a king bed, two twin beds, a living area with TV, wet bar, walk-in closet, and full bathroom. There is also a flexible sixth room that can be used as a playroom, home office, or reading and study space depending on your group’s needs. All bedrooms feature Casper mattresses, organic cotton linens and towels, down duvets, and blackout window treatments to ensure restful sleep.brbrKitchen & Dining:brThe kitchen is fully equipped for both casual family meals and entertaining. Highlights include a professional Wolf gas range, GE Monogram refrigerator, wine fridge, and a complete collection of premium cookware and small appliances. Guests can enjoy meals across four dining spaces—two indoors and two outdoors—including a main outdoor dining deck with a Weber Genesis gas grill and side burner. A side patio with a hanging rattan chair offers a quiet spot for morning coffee or afternoon reading.brbrDesigned for Families — and Flexible for Adult Groups:brThe home includes a versatile flex space designed to adapt to your stay. For families, it functions as a playroom with toys, books, art supplies, and a TV. For adult groups or remote-friendly stays, it can easily be used as a quiet home office or reading lounge, complete with a built-in bookcase and comfortable seating.brbrFor those traveling with children, the estate offers exceptional kid-friendly amenities. Outdoors, the private playground features swings for various ages, a climbing wall, slide, monkey bars, sand pit, and a hidden picnic nook. Beach toys, a beach wagon, and cribs (available upon request) make traveling with little ones easy and stress-free.brbrLiving & Gathering Spaces:brThe main level features a bright, open living room alongside the eat-in kitchen and formal dining room, creating seamless flow for gathering. A mudroom with laundry and multiple powder rooms add everyday convenience. Upstairs, a dedicated media room with a large sectional is perfect for movie nights or quiet downtime.brbrLocation & Walkability:brLocated in Southold on the North Fork of Long Island, the estate is within a 10-minute walk to Kenney’s and McCabe’s beaches, as well as the newly opened Little Fish restaurant at Kenney’s Beach. Horton’s Point Lighthouse is an easy walk, and many of the North Fork’s best wineries, farm stands, restaurants, and additional beaches are within a short drive. The home is approximately two hours from New York City, making it an ideal summer escape without the hassle of long travel.brbrIdeal For:brThis home is best suited for families and multi-generational groups, friends vacationing together, guests seeking privacy and walkable beach access, travelers looking for a refined and relaxed North Fork experience, and remote-friendly stays with space for work or quiet reading.

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Bath

Sleeps

$1501.07

/ Nightly

Private Vacation Home

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold, New York, United States

Town of Southold Rental Permit Number 0816 A beautiful brand new estate home with a heated pool, situated in the heart of picturesque North Fork. Minutes from wineries and Goose Creek Beach, steps from a small private creek beach. With 6000 sq feet, 8 spacious bedrooms and 7 full bathrooms, this home was built for entertaining and enjoying time with family.brThe chef's kitchen with top of the line appliances is perfect for cooking up meals for large gatherings. 2 Dishwashers and 2 sets of washer/dryer units make the cleaning part a breeze. A wet bar with a beverage refrigerator is perfectly located by the large fireplace which anchors the large open concept living space.brThe lower level provides an additional space for family fun - a convertible pool/ping pong table and a kitchenette make it perfect for kids. brThe backyard boasts a 20 by 40 salt water pool with a retractable cover, plus a beautiful pool deck with lots of seating and umbrellas - all a perfect set up for outdoor living.

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Bath

Sleeps

$2690.69

/ Nightly

Private Vacation Home

Contemporary Colonial home with pristine Peconic bay views, Heated...

Southold, New York, United States

Vineyard Beach HousebrbrContemporary Colonial home with pristine Peconic bay views, Heated saltwater pool, steps to private beach, Weber grill, fire pitbrbr4BR/3.5BA - open floor plan, soaring ceilings, two-story living with cozy den and fireplace, floor-to-ceiling windows, two Primary suites and one with a private deck, large social kitchen, Sonos systembrbrTimeless North Fork charm meets elevated coastal living. Welcome to this four-season seaside retreat, where sweeping Peconic Bay views and the soothing rhythm of the water set the tone for your stay. Just steps from the beach and minutes to town, youre perfectly positioned to enjoy the North Forks best boutiques, restaurants, and renowned vineyards.brbrSpanning over 3,200 square feet, the home offers a sun-drenched, open layout with effortless flow and striking architectural details, including soaring ceilings and walls of windows that frame the water from nearly every angle. The two-story living room is both grand and inviting, complemented by a cozy den with a stone fireplaceperfect for cooler evenings.brbrThe bright, eat-in kitchen is fully equipped for everything from casual breakfasts to larger gatherings, with ample seating for entertaining. Just beyond, a tranquil sunroom provides the perfect space to unwind. Four serene bedrooms and two-and-a-half well-appointed baths complete the home, including a stunning primary suite with panoramic bay views, a king-sized bed, private deck access, and a spa-like ensuite.brbrStep outside to an expansive deck ideal for lounging and al fresco dining, or enjoy the homes newest highlight: a heated saltwater pool, offering a private resort-style experience throughout the season.brbrDirectly across the street sits The Old Field vineyard, with over 40 wineries and several microbreweries nearby. From farm-to-table dining to laid-back coastal living, this is North Fork at its finest.brbrPlease note: the dock is currently unavailable for use.brbrThis property has a max occupancy of 10brbrBedroomsbrbrPrimary Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/DeckbrbrBedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Standard Closet, Balcony/DeckbrbrAdditional Sleeping Area: Two Twin Single Beds, 2nd Floor, Air ConditioningbrbrBathroomsbrbrBathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, TubbrbrBathroom 2: Full Bath, 2nd Floor, Shower/Tub CombobrbrBathroom 3: Full Bath, First Floor/Main Floor, Ensuite, ShowerbrbrBathroom 4: Half Bath, First Floor/Main FloorbrbrTVsbrbrPrimary Bedroom 1: StreamingbrbrOutdoors & Pool/SpasbrDeck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Balcony, Bicycle (4 Adult Bikes, 4 Children Bikes), Beach Chairs (8 Chairs), Beach Umbrella, Kayak/Canoe, Paddle Board, Private Pool (Outdoor, Heated, Saltwater)brbrAmenitiesbrBed Linens, Bath Towels, Iron/Ironing Board, Washer, Dryer, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Private Entrance, Parking (2 Cars In Driveway), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Pool/Beach Towels, Hair Dryer, Air Conditioning (Central Air), Usable Fireplace (Wood-Burning), Wine Fridge, Ice Maker, Coffee (Pot, Nespresso), Toaster, Blender, Television (Main Living Room, Kitchen, Den), Cable TV, Smart TV, Speaker System (Sonos), Laptop-Friendly Workspace, Pots and PansbrbrOther FAQ'sbrbrPool Fenced In: NobrbrBackyard Fenced In: YesbrbrEstimated Square Footage: 3,500brbrSuitability: Not handicap accessible.brPrimary renter must be at least 25 years old.brbrPet Policy: Pets are strictly prohibited at this property.brbrUtility Disclaimer:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $80.00 per night 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: No additional guests beyond the max occupancy of this listing are permitted.brbrEvents Policy: Events are prohibitedbrbrSpecial 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.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.

Bed

Bath

Sleeps

$1079.6

/ Nightly

Private Vacation Home

Southold Escape with Large Saltwater Pool on Wine Trail

Southold, New York, United States

3 bedroom, 2.5 bathroom home on a 0.55 acre property with large pool and outdoor deck in enclosed private backyard. Brand new wooden playset and seesaw for families with young children to enjoy.brEscape from it all.....here on the North Fork. Its near the beach and vineyards and feels like a private retreat.brWhether for a family retreat or couples escape this is perfect and best of all just under 1 1/2 hour drive from the city!brIf you are interested in a private getaway that far exceeds other listings just contact us and we can work together planning your getaway! Minimum stays required. We comply with local codes.brThe house is super comfortable with central air conditioning and heat as needed.brMake yourself at home this summer in a spacious and beautiful North Fork Wine Country home in Southold! Comfortably sleep six to eight people in this 1,800 sq. ft. home with three bedrooms, two couches, an air mattress and two and a half baths. The kitchen and dining area have a view of the deck that overlooks the enclosed backyard with the pool. Relax in the living room or family room or respond to some e-mails in the master bedroom which has a desk for added privacy. brThe deck has ample seating in the form of a teak table with cushions that can be found in the two deck boxes and a sectional with lounge chairs to enjoy the the pool while cooking up some burgers on the grill, and winding down for the night on the patio or roasting marshmallows on the fire pit. brThe North Fork has plenty of beautiful sights and activities for you to enjoy. Walk down the road to The Old Field Vineyard for a wine tasting, hop in the car and head to the Village of Greenport (about 4 miles away) to enjoy their many restaurants and boutiques along the harbor. Plan a trip to Shelter Island, Sag Harbor, and the Hamptons via the North and South Ferries! There are plenty of nearby North Fork beaches along either the Long Island Sound or Peconic Bay to enjoy.brThis home is a perfect spot for a relaxing, dreamy North Fork escape!If you get bored of the activities on the property, you will be located a short drive away from some of the best vineyards on the North Fork, the famous Love Lane, Beaches on the Long Island Sound as well as Peconic Bay. There is plenty of shopping in Southhold, Mattituck, Greenport Town and Tanger Outlets in Riverhead with countless little shops filling the space between.

Bed

Bath

Sleeps

$1340.45

/ Nightly

Private Vacation Home

Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...

Southold, New York, United States

Please note that a reservation for this property needs to be approved before it is confirmed.brbrNorth Fork FarmhousebrbrExpansive North Fork Estate on almost 3 Acres, Close to Vineyards and Beaches, Perfect for Familiesbrbr5BR/3.5BA: private heated pool, outdoor shower, outdoor dining, fire pit, swing set, multiple sitting and dining areas, total privacybrbrNestled in the charming town of Southold, this contemporary horse farm estate offers a peaceful retreat for families and friends. With an open floor plan, five beautifully appointed bedrooms, and 3.5 bathrooms, this spacious home accommodates up to 10 guests comfortably. The property is bright and airy, featuring multiple sitting and dining areas that invite relaxation and connection. Whether youre seeking a tranquil getaway or a space to gather with loved ones, this estate provides the perfect setting to escape daily life. Surrounded by natural beauty and just minutes from local beaches and town amenities, it combines modern comfort with a touch of rustic charm.brbrStep outside to discover an array of exterior amenities designed to help you unwind. The property ensures complete privacy, with an expansive deck outfitted with a dining table and multiple seating areasperfect for morning coffee or evening cocktails under the stars. The sprawling yard features a private heated pool for refreshing swims, a cozy fire pit for storytelling and smores, and a swing set for children to enjoy. An outdoor shower offers convenience after beach trips, while the gas BBQ invites al fresco dining experiences. With plenty of free parking, this estate ensures both convenience and luxury for every guest.brbrFrom the moment you enter, this home enchants with its open layout and abundant natural light. Central air conditioning ensures year-round comfort, while high-speed WiFi keeps you connected. Flow effortlessly between the spacious living room, elegant dining room, and gourmet island kitchen. The kitchen is a chefs dream, boasting top-of-the-line appliances, a coffee maker, and ample counter space for culinary creations. A dedicated work-from-home space makes it easy to balance leisure with productivity. Throughout the home, large windows frame stunning views of the surrounding horse farm, creating a serene and picturesque backdrop.brbrEach of the five bedrooms is a haven of comfort, featuring fresh linens and all the essentials you need for a restful stay. The primary suite boasts an en-suite bathroom with a spa-like ambiance, while the additional bedrooms and bathrooms are equally well-appointed to accommodate every guests needs. Whether youre waking up to gentle morning light or unwinding after a day of exploring, these spaces ensure you feel right at home.brbrConveniently located near the towns of Cutchogue, Peconic, and Greenport, this property is your gateway to the best of the North Fork. Explore a variety of local wineries, farm stands, and fine restaurants, or immerse yourself in the regions rich culture with visits to art galleries and antique shops. From sandy beaches to charming boutiques, theres something for everyone just a short drive away.brbrThis Southold estate offers an unparalleled combination of luxury, privacy, and proximity to the vibrant offerings of the North Fork. Whether youre planning a family vacation, a getaway with friends, or a special celebration, this home is the perfect setting for unforgettable memories.brbrThis property has a max occupancy of 12brbrBedroomsbrbrBedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 2: One Bunk Bed, One Crib Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 3: One King Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrPrimary Bedroom 4: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Standard ClosetbrbrBedroom 5: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, ClosetbrbrBathroomsbrbrBathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, TubbrbrBathroom 2: Full Bath, 2nd Floor, Shower/Tub CombobrbrBathroom 3 Primary: Full Bath, 2nd Floor, Ensuite, ShowerbrbrBathroom 4: Half Bath, First Floor/Main FloorbrbrOutdoors & Pool/SpasbrDeck/Patio (Uncovered), Outdoor Shower (Hot + Cold Water), Patio Furniture (Table, Chairs, Umbrella), Fence Around The Pool, Fence Around The Yard, Fire Pit (Wood-Burning), Swing Set, Grill (Gas), Lounge Chairs (6 Chairs), Private Pool (Heated, Saltwater)brbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television, Private Entrance, Parking, Smoke Detector, EssentialsbrbrLocationbrbrNearby Beaches:brHorton 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 MuseumbrbrRental Registration: 1241 expires on 12/17/2026.brbrSuitability: Not handicap accessible.brPrimary renter must be at least 25 years old.brbrPet Policy: Pets are strictly prohibited at this property.brbrUtility Disclaimer:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $75.00 per night 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.brbrEvents Policy: Events are prohibitedbrbrSpecial 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.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.

Bed

Bath

Sleeps

$850.75

/ Nightly

Private Vacation Home

Bayfront Vacation Home in Southold, 5 Bedrooms

Southold, New York, United States

Take in the extensive views from this lovely Goose Creek Front waterfront vacation home, with private deck and beach. Top rated Southold beach destination just across the street and close to the Southold Yacht Club on the bay. Explore the North Fork from a different vantage point; rent a boat from Strong's Marina dock it at the house, or take to the lagoon on our one of two kayaks. Enjoy the fire pit with family/friends on our private beach.brbrThe main level bedrooms, on second floor, feature a King ensuite master bedroom and the second bedroom contains a King size bed. Also, there are two full bathrooms on this floor. The main living area offers a modern kitchen, living room, and dining with 180 degrees views of the water (via an outside balcony). Take advantage of the flow onto the shaded deck with picture perfect views. Entertaining spaces inside and out!brbrThe first floor offers two bedrooms, one with a bunk bed of 3 full-size beds and the second room with a Queen size bed, as well. Also, the is a full bathroom, living room, and updated bar area.brbrThe attic offers 2 queen size beds. It is equipped with a TV, an additional AC unit and a sun-window.

5

Bed

3

Bath

8

Sleeps

$977.03

/ Nightly

Private Vacation Home

North Fork Waterfront Gem!

Southold, New York, United States

Live the waterfront life! Kayak, paddle board, boat from your front door! Enjoy gathering your own oysters and clams from your waterfront backyard! Walking distance to Sound Beach, 5 minute drive to bay beach. Surrounded by vineyards and farm stands, this is the best of the North Fork!brIncludes kayaks, paddle board, bicycles, beach equipment and even a clam rake!

Bed

Bath

Sleeps

$954.93

/ Nightly

Private Vacation Home

Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!

Southold, New York, United States

Enjoy the NOFO life - full of farm to table food, amazing oysters, and beaches! brbrThis newly renovated stylish house sleeps up to 12 and is the perfect quiet retreat - a pool, a hot tub and all on a quiet street just minutes from Goose Creek Beach, the adorable Croteaux Winery, Southold General, the Southold Fish Market, several farm stands and North Fork Table and Inn. brbrThis house was recently renovated and decorated and every sofa, lamp and bed are brand new. The property has every amenity for a relaxing getaway - lounge chairs, outdoor dining table, hot tub, pool, outdoor grill, toys for the kids - you name it - all in a secluded spot on a quiet cul-de-sac. brbrPeace and relaxation are yours to be had in this little sanctuary - we hope you love it!brbrAmenities include, but are not limited to:br- 4 bedrooms (1 king, 2 doubles, 1 kids room with twin and bunk + trundle)br- 3 full bathroomsbr- propane gas grillbr- firepitbr- outdoor lounge chairsbr- porch swingbr- smart TVs (70' and 45') with Netflix, Hulu, Amazon, etc.br- Google Homebr- washer & dryerbr- Wifi includedbr- concierge garbage pick-upbrbrbr- Dogs allowed for an additional fee ($150/dog)br- No smoking permittedbr- located in quiet cul-de-sacbr- Town beach parking permits available for stays of 30 days or longerbrbr

Bed

Bath

Sleeps

$924.06

/ Nightly

Private Vacation Home

Luxury by the Sea

Southold, New York, United States

Your search is over! Brand New Construction. Charming, luxurious, private, comfortable Beach House. Stunning 3 bedroom 21/2 bath house on fully fenced in 1.25 lush acres. br King size master with gorgeous en-suite has separate soaking tub and spa shower . This home is beautifully designed with too many architectural details to list with amazing detail and craftsmanship. br Property is fully furnished with no detail spared . Open floor plan, spacious great room with gas remote controlled fire place and flat screen, and gourmet eat in kitchen with large island is a wonderful place to entertain . br Brand new washer/dryer, butlers pantry and mud room. Attached 1 1/2 car garage with plenty of storage. Plenty of parking. br Where the country meets the sea enjoy all the North Fork has to offer. You’re in the middle of beach and Wine Country with tons of vineyards and local farms to explore. Beautiful beaches are 2 min away in any direction. br Close to the Tanger outlets and so many other shops in beautiful Riverhead as well as the Aquarium. You can also take a 10 min drive to beautiful Greenport or hop on the ferry to Shelter Island. br So much to do or just stay home relax and enjoy the beautiful tranquil patio, new Weber BBQ with its own gas⛽️ line and beautifully landscaped enclosed yard. br You will not be disappointed. All beach gear, 4 beach chairs, 2 coolers, beach umbrellas ⛱, wagon etc are included with your stay!!br The only thing missing is YOU… br

Bed

Bath

Sleeps

$3433.23

/ Nightly

Private Vacation Home

Luxury north fork estate

Southold, New York, United States

Absolutely stunning custom home Italian Tuscan style villa on the outside. Modern Hamptons vibe on the inside . 1 acre + gated private compound with amazing Infiniti edge salt water pool and oversized spa. Outdoor patio with outdoor wood burning fireplace . Admire the vineyard on the hill or the help yourself garden with all fresh organic vegetables and herbs, outdoor wood burning pizza oven .

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$559.01

/ Nightly

Private Vacation Home

Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach

Southold, New York, United States

This is a Spacious & Meticulous Cape On Great Hogs Neck Peninsula ~ This Charming 4-Plus Bedroom 3.5 Bath Expanded Cape Has Ample Room With Its 2 Large Suites Plus 2-3 More Bedrooms, 3 Full Baths, 1 half bathroom, A Generous Formal Dining Room, Roomy Living Room With Fireplace & Comfortable Eat in Kitchen that leads out to an oversized deck with grill. Bar, pool table, and large surround sound tv! Close To Numerous Great Beaches, Restaurants, Vineyards & Fun Activities For All!

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$293.9

/ Nightly

Private Vacation Home

Lake House Located Near North Fork Wineries

Southold, New York, United States

This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Barbecue and dine in the spacious backyard with a sunset view of the lake. Stargaze with no interfering city street lights. House has two bedrooms accommodating up to four people, a large ranch-style kitchen with dishwasher, microwave and coffee maker, wifi internet access, A/C, and a TV, and DVD player. Pets allowed with prior approval. *TWO WEEK MINIMUM*brbrThis beautifully landscaped property is one half acre in size with wooded and open areas and a private bulkheaded lakefront. It is ideal for families with young children who like to explore. The house comes completely furnished, with the exception of towels and linens.brbrJust down the road at the end of the lake is Peconic Dunes Camp, a summer camp operated by Suffolk County. The village of Southold is just a five minute drive away, as well as 20 of the North Fork's finest wineries. Other local visitor attractions include the historic port villiage of Greenport, Horton's Point Lighthouse, and Goldsmith's Inlet County Park.

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$523.12

/ Nightly

Private Vacation Home

House of Classic Arts and Crafts North Fork

Southold, New York, United States

This charming Southold village house sits on a half acre with a back deck overlooking a sweeping backyard. Newly furnished and freshly painted, it is centrally located to wineries, bay and sound beaches and is a short walk to shops. Enjoy the sunset on the deck or in the hammock and maybe get a glimpse of a deer family that often walk by. Come enjoy all that the wonderful North Fork has to offer! brbrTaxes: as of 2023, Suffolk County is requiring us to charge 5.5% tax per booking, please note this is in addition to State of New York sales tax of 8.625%, hence the total taxes due are bundled together for a total of 14.125%....br

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$3384.82

/ Nightly

Private Vacation Home

HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

Southold, New York, United States

Brand new heated gunite saltwater pool!!!!brA sparkling clean and modern 6 bedroom, 4 bath waterfront home offering all the luxuries you'll want and more for your North Fork vacation. Private 6 acre property features gorgeous water views, long dock for your boat, kayaks, stand up paddle boards, large firepit area, bicycles, a 2600 square foot deck perfect for lounging and dining with brand new heated saltwater gunite pool, lounge chairs, sun beds, covered daybed, dining table for 12, full chef’s outdoor kitchen, a top of the line hot tub for 6 adults, and a private outdoor shower with rain shower head and excellent water pressure. Swimming, fishing, and crabbing right off the long private dock. Indoors you will find an enormous fully stocked eat-in kitchen with sliders to the deck, beautiful dining room for 12, large living room with grand fireplace and TV, main-level gym with smart bike, workout Mirror, and gorgeous views, master bathroom with double shower head, sauna for 2, and large jacuzzi; separate kids’ space that sleeps 4 with en-suite bathroom, sectional sofa, and TV. Boat, paddle, bike or drive to 4 separate beaches that are 2-4 minutes away, or enjoy multiple vineyards, award winning restaurants, and fresh produce, meats, and fish from the local farms and farm stands a stone’s throw away along with the beautiful towns that the North Fork has to offer.

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$692.38

/ Nightly

Private Vacation Home

Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views

Southold, New York, United States

Summary:brbrWaterfront home on Goose Creek in Southold with a private dock, kayaks, and large backyard to the water. Three bedrooms, two full bathrooms, and an open-plan living area on a single level with no stairs. Wood-burning brick fireplace, deck with dining and grill, and outdoor shower. Pet-friendly with feebrbrbrbrThe Space:brbrThe main level has an open kitchen, dining area, and living room with hardwood floors throughout. The kitchen has dark wood cabinetry, stainless steel appliances, a peninsula with bar seating, and a sliding glass door to the rear deck with water views. The dining table seats six under a chandelier. The living room has a wood-burning brick fireplace, TV, and ceiling fan.brbrbrbrThe primary bedroom has a king bed with an accent wall. The second bedroom has a king bed. The third bedroom has two twin beds. Both full bathrooms have tub or shower and single vanity. In-unit washer and dryer. Central air conditioning.brbrbrbrThe rear deck overlooks the yard and Goose Creek with dining seating for four, Adirondack chairs, and a Weber gas grill. The yard extends to the water with a private dock (accommodates boats up to 25 feet) and kayaks. A fire pit and outdoor shower are on the property. brbrbrbrSeasonal Availability of Outdoor AmenitiesbrbrOutdoor amenities, including patio furniture and grills, are typically stored between Columbus Day and Memorial Day. Contact us with questions about specific amenities during your stay dates.brbrbrbrIMPORTANT NOTES:brbr• Primary renter must be 25 or olderbrbr• Standard pet fee of $200 per pet, per stay. An additional $100 may apply for dogs that shed excessively.brbr• No smokingbrbr• For stays over 21 days, excess utility costs beyond the base allowance are the guest’s responsibilitybrbr• Reservations of 29 nights or more require a refundable security depositbrbr• Rental Permit #0715brbrbrbrGuest Access:brbrFull private access to the home, deck, yard, dock, and kayaks. On-site parking. Check-in instructions provided prior to arrival.brbrbrbrThe Neighborhood:brbrSouthold is on the North Fork of Long Island with vineyards, farm stands, and creek and bay beaches within a short drive.brbrbrbrNearby:brbr• Goose Creek Beach – 1.1 miles (walkable or 3-minute drive)brbr• Sparkling Pointe Vineyards – 4-minute drive (1.9 miles)brbr• Southold Village – 5-minute drive (2 miles)brbr• Country View Farm Stand – 5-minute drive (2.3 miles)brbr• The Old Field Vineyards – 5-minute drive (2.7 miles)brbr• Macari Vineyards – 8-minute drive (4 miles)brbr• Greenport Village – 8-minute drive (5 miles)brbr• Harbes Family Farm – 12-minute drive (6 miles)brbr• Orient Beach State Park – 18-minute drive (10 miles)brbrbrbrGetting Around:brbrA car is recommended. Vineyards, farm stands, restaurants, and beaches are within a short drive. The Southold LIRR station is approximately 2 miles from the property. Hampton Jitney service is available seasonally.brbrbrbrOther Things to Note:brbrCancellation PolicybrbrBookings canceled at least 30 days before the start of the stay receive a 100% refund. Bookings canceled at least 14 days before the start of the stay receive a 50% refund.brbrbrbrGuest InsurancebrbrGuests are required to sign a Rental Agreement. A property damage protection policy is included with the booking for stays less than a month. This policy covers incidental damage to the home during the stay. It does not cover trip cancellation due to illness or other personal reasons. Report any incidents to our team promptly. Longer stays require a refundable damage deposit. brbrbrbrOur CompanybrbrLuxury Beach Getaway has offered curated vacation home rentals in the Hamptons and North Fork since 2008.brbrbrbrInteraction with Guests:brbrWe provide contactless check-in and are available by phone or message throughout your stay. Our local team is nearby if assistance is needed.

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$519.7

/ Nightly

Private Vacation Home

Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries

Southold, New York, United States

Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood, minutes from northfork's greatest attractions and entertainment. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen with new appliances, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. The rooms are beautifully decorated with original art sourced locally and globally adding color to your stay. Outside, a savor al fresco dining amid the lush greenery surrounding the screened in porch and brick patio with outdoor dining area and gas BBQ. Whether you are hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. Popular beaches, restaurants, and wineries are all close by. Do not miss your chance to experience the best of Southold living

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$778.65

/ Nightly

Private Vacation Home

Steve’s Place | Heated Pool, Fenced Yard & Quiet Southold Setting

Southold, New York, United States

Summary:brbrSteve’s Place is a comfortable Southold home with a private heated pool, fenced yard, and inviting outdoor living areas. The home offers three bedrooms and one and a half baths, sleeping up to six guests, and is well suited for family stays and longer summer visits. Enjoy a fully equipped kitchen, cozy living room, and covered outdoor dining overlooking the pool. Located in a quiet neighborhood close to beaches, vineyards, and North Fork farm stands.brbrbrbrThe Space:brbrVRBO guests: This home is ideal for families or small groups seeking a quiet North Fork base for a longer stay. The fenced yard and heated pool provide privacy and space to relax, while the interior layout offers comfortable shared living areas and simple, functional bedrooms. Outdoor amenities are seasonal; please review availability details below.brbrbrbrSteve’s Place is a comfortable and well-maintained Southold home designed for relaxed family stays. The home sleeps up to six guests across three bedrooms, with two queen beds and one bunk bed with a full-size lower bunk.brbrbrbrInside, the remodeled kitchen is fully equipped and opens to a cozy living area with ample seating, making it easy to spend time together after a day at the beach or vineyards. The living room is ideal for movie nights, reading, or quiet evenings in. The home is pet-friendly for small dogs, allowing the whole family to travel together.brbrbrbrOutdoors, the fenced yard is a private retreat featuring a heated pool, poolside loungers, a gas grill, and covered deck seating with views of the pool and garden. The setting is quiet and residential, offering a calm place to unwind while remaining close to everything Southold and the North Fork have to offer. For safety purposes, a pool fence has been installed around the pool. Please note that the fence is not shown in the current listing photos.brbrbrbrRental Permit #0759brbrbrbrSeasonal 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.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 NOTES:brbr- The primary renter must be at least 25 years old.brbr- There is a standard pet fee of $200 per pet, per stay. An additional $100 may apply for dogs that shed excessively. (We only allow small dogs)brbr- For stays over 21 days, please note that any extra utility costs beyond the initial charged amount are the guest's responsibility.brbr- Properties with a heated pool incur a daily pool heat fee of $45.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- Sparkling Pointe Vineyards and Winery (2.3 miles)brbr- Showcase Wine and Liquor (3.2 miles)brbr- Slice of 48 (3.2 miles)brbr- Country View Farm Stand (3.2 miles)brbr- The Old Field Vineyards (3.5 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.brbr- Please note: This cancellation policy is not applicable for HVMB guests.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

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Vacation Home Rentals By Owner In Southold, NY

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