Home Vacation Rentals By Owner In Southold, NY

Showing 80 Of 99 Vacation Rentals
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Exceptional(42)

$874.78

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Private Vacation Home

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold, New York, United States

Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New York has to offer!brbrAnd welcome to our home: a fully-renovated, brand new everything stylish retreat located in Southold—just minutes from Goose Creek Beach, North Fork Roasting Company, Southold Fish Market and Corey Creek Winery. brbrEvery inch of the house and its furnishings are brand new. It features tons of natural light via vaulted ceilings and multiple skylights throughout the living, family and kitchen areas. With an open concept, this property offers the perfect space for families looking to entertain, dine, grill and enjoy the peacefulness of this cul-de-sac property. brbrThe house has been curated with love and we hope you enjoy it as much as we do!brbrAmenities include, but are not limited to: br- 4 bedrooms (1 king, 2 queens, 2 twins) br- 2 full bathroomsbr- propane gas grillbr- firepitbr- Adirondack chairs br- outdoor shower br- outdoor dining roombr- outdoor lounge areabr- smart TVs (70' and 55') with Netflix, Hulu, Amazon, etc.br- Google Homebr- washer & dryer br- Wifi includedbr- concierge garbage pick-upbr- queen blow-up mattressbrbr- Dogs allowed for an additional fee ($150/dog)br- No smoking permittedbr- located in quiet cul-de-sac br- Town beach parking permits available for stays of 30 days or longerbr
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$160.79

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Cottage

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold, New York, United States

If you’re a nature lover, a beach lover, a wine lover, or just in need of an escape, plan your dates for a stay at this 2-bedroom, 1-bath cottage in Southold! Reconnecting with Mother Nature is made possible during your stay at this rustic vacation rental that offers a well-equipped kitchen, a screened-in porch, and a grill for barbecues! Walk down the road for a day at the beach, tour the myriad of local wineries, and spend time with family or friends on Long Island’s North Fork.brbr-- THE PROPERTY --brbrWood-Burning Fireplace | Screened Porch | Free WiFi brbrBedroom 1: Full Bed | Bedroom 2: Full Bed | Living Room: FutonbrbrINDOOR LIVING: Dining table, ceiling fans, board games, booksbrOUTDOOR LIVING: Outdoor dining set, gas grill, patiobrKITCHEN: Stove/oven, microwave, refrigerator, drip coffee maker, slow cooker, toaster, cooking basics, dishware/flatware, trash bags/paper towelsbrGENERAL: Portable A/C units, linens/towels, complimentary toiletries, hair dryerbrSUITABILITY: 2 steps required to access, single-story homebrPARKING: Driveway (3 vehicles)brbr-- THE LOCATION --brbrPARKS & BEACHES: South Harbor Park (0.4 miles), Sound View Dunes Park (4 miles), Mashomack Preserve (11 miles)brWINERIES: Croteaux Vineyards (0.5 miles), Duck Walk Vineyards (1 mile), Sparkling Pointe Vineyards & Winery (2 miles), Lenz Winery (2 miles), Bedell Cellars (3 miles), Pindar Vineyards (3 miles)brATTRACTIONS: Southold Indian Museum (0.9 miles), Custer Institute and Observatory (0.9 miles), Horton Point Lighthouse Nautical Museum (4 miles), Antique Carousel (7 miles)brAIRPORT: John F. Kennedy International Airport (88 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are 2 steps required to enter
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Exceptional(20)

$443.2

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Private Vacation Home

Waterfront, New Construction North Fork Beach House

Southold, New York, United States

Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction (2014) 2,000 sq.ft. home exudes that coastal New England summer vibe. Its waterfront location allows for endless swimming, paddling and watersports right outside your door. Start your day early with a paddle on tranquil Goose Creek or soak up some rays in the sand and on comfy lounge chairs. Alternatively, bring your own boat or rental for longer excursions to Peconic Bay, Greenport, Shelter Island, Sag Harbor and more.brbrAfternoon plans can include a visit to one (or several) of the many excellent wineries dotting the North Fork or nearby Greenport Harbor Brewing (15 options within 5 miles). Stroll through the quaint village of Southold (founded 1640, oldest English settlement on Long Island) or the bustling seaport of Greenport and discover the region’s growing arts scene, exploding artisanal foods options and wonderous farm stands. You’ll soon have your favorite vineyard, farm stand, cheese place, coffee roaster and personal oyster supplier… and there goes the afternoon.brbrAlternatively, pick up your shellfish permit and go clamming right off the dock outside the house. Be sure to be back in time, however, to enjoy the epic sunsets from the expansive deck and/or balcony while you savor your local wines, specialty cocktails and masterful BBQ. Finish the evening off by gathering your group around the firepit for s’mores and a nightcap.brbrYour accommodations include: 4 bedrooms, 3-1/2 baths. BR1 - Lower Master (Queen bed); BR2 - Kids’ Quarters (2 bunk beds); BR3 - Upper Master w/ en-suite bath; BR4 - Bed/Office w/ en-suite bath. Lower level has a shared full bath and a shared half-bath.brbrThe open plan kitchen/dining/living area boasts gorgeous, length-of-house water views that bring the outside in. And with a true chef’s kitchen at the ready, it will be a breeze turning all that North Fork deliciousness you’ve scooped up into an impressive meal. Features include a commercial-grade 6-burner stove/oven, oversized island with generous counter space and seating, wine refri and beverage center, quality cookware and cutlery, and much more.brbrFeatures & Amenities:brbrWaterfront; Sandy beach barrier w/ lounge chairs and Adirondacks; Boat dock; Kayaks; Firepit; Outdoor grill/BBQ; Deck/Patio; Air conditioning; Fireplace; Full Kitchen; Commercial oven/stove; Microwave; Wine refri; Beverage center; Dishwasher; Laundry machines (Washer/Dryer); Cable TV & Streaming devices; Internet/WiFi; Balcony; Queen-sized beds with new memory foam mattresses; Bunk beds in kids’ room; Bed linens and bath towels provided; brbr-- POLICIES --br- Southold Town Rental Permit #0229br- Min. 2 week rental (as per Southold Town law)br- No smokingbr- No pets allowed without prior approvalbr- No events, parties or large gatherings (max. 8 occupants at all times)br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID required to confirm booking and upon check-in
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Exceptional(19)

Select Dates for Price
Private Vacation Home

Waterfront, private beach, ready for adventure, light & bright!

Southold, New York, United States

Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, this light and airy 4 bedroom, 2.5 bath property is the perfect North Fork retreat! Coastal furnishings, with a large deck and grounds, enjoy paddle boarding, kayaking, and swimming right from your own beach. Or take a bike ride or short drive to hamlet shopping, restaurants, transportation, award winning wineries, and Peconic Bay and Long Island Sound beaches. The ultimate North Fork vacation awaits!br4 Bedrooms, 2.5 baths, 3200 square feetbr• Great room with cathedral ceiling and direct views of Long Creekbr• Family room/den with 65” smart TV with Netflix/Amazon/Disney access and 1 Gbps wireless Internet (includes Eero mesh network for full house/deck WiFi coverage and 3 desk work spaces)br• Newly renovated well-equipped kitchen with eat-in counter space including new gas Wolf 6-burner range and built-in Bosch dishwasher, refrigerator and speed oven.br• Dining area off Great Room with direct access to deck and stunning views of Long Creekbr• 540 square foot wooden outdoor deck, new Fortunoff outdoor teak dining furniture, 3 umbrellas and Weber propane grillbr• 1st floor Primary Room with king bed, smart TV and two walk-in closets, ensuite bathroom with jacuzzi tub, twin sinks and walk-in showerbr• Separate powder roombr• New 1st floor washer/dryer in mud room with access to garagebr• 2nd floor King Bedroom with smart TV and water views in two directionsbr• 2nd floor Queen Bedroom with optional extra twin bedbr• Separate 2nd floor bunk room with 4 twin beds and walk-in closetbr• 2nd floor full bath with twin sinks and separate room for toilet and bath/shower.brOther:br• BYO dinghy or kayak, steps down from property to beach and Long Creek accessbr• Great walking/biking neighborhood for the familybr• Potential access to Kenney's Beach, Goose Creek and Southold Town Beachbr• Outdoor deck chairs, 4 Polywood Adirondack chairs, 2 teak recliners, outdoor 8 person teak dining set with oversized umbrella, two other family seating areas on deck, fire pit, wide hammock and separate kid picnic table.br• Baby crib, Pack-n-Play and bedrails availablebr• 1 mile to Southold Village (easily accessible on foot or bike)br• Walk/bike access to local vineyards, farm stands and fresh seafood marketbr• Additional kayaks, sail and power boats available for rent at nearby Port of Egyptbr• Hampton Jitney Stop and Southold train station less than 5 minute drive from housebr• Greenport Village with ferry to Shelter Island ~ 3 miles eastbr• Orient Point with ferry to New London ~ 12 miles eastbrTwo-week minimum by town ordinance.brCleaning fees, security deposit and insurance required.
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Exceptional(6)

$1652.12

/ Nightly
Private Vacation Home

5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..

Southold, New York, United States

Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/3.5 bath newly renovated expansive modern contemporary property. This property is located steps away from a sandy private beach facing Shelter Island and across from a well known North Fork vineyard. This property is perfect for families to enjoy as it is located on a quiet dead end street. This will be a vacation that will surely not be forgotten as it is quite a magical place!brbrRelax in a newly appointed master bedroom with stunning views of the Peconic Bay from a private terrace. A plush, king-sized bed with armoire and private on-suite bathroom makes this master bedroom a quiet retreat like no other. brbrThe home bodes an additional master suite located on the ground level with a Queen-sized bed, on-suite bathroom and it's own separate entrance. There are 2 additional bedrooms, each with a Queen sized bed and one bedroom with 2 twin sized beds making this home comfortable for 10 guests. Imagine cooking meals with locally grown organic vegetables, eggs or the fresh catch of the day from the nearby fish market in the large contemporary kitchen perfect for entertaining. The kitchen is equipped with top of the line stainless steel appliances, a wine cooler and beverage center, oversized sub-zero fridge, Wolf cook top and double wall oven. There are 8 stools surrounding the L-shaped island perfect for enjoying time with family and friends. brbrThere is a beautiful sun room equipped with ample soft plush seating, smart flat screen TV for entertainment and with glass doors leading to an outdoor deck. The house is equipped with Wifi, brand new indoor/outdoor Sonos sound system, central A/C and heating, cable TV and access to movie channels. There are 2 additional living spaces; a warm and cozy family room with oversized fireplace, 65 inch smart TV and sliding doors also leading to the outdoor deck with oversized outdoor table seating 10 people, stainless steel Weber BBQ, fire pit additional bar table and stools for extra guests. brbrThe living room located in the front of the house has cathedral ceilings with white wooden planks and oversized windows making it a perfect sitting area to enjoy your favorite glass of wine. Across the way from the living room, guests have access to a cleanly furnished dining room with views of the neighboring vineyard. brbrThe home comes complete with linens, beach and bathroom towels, beach chairs and umbrellas and laundry room with brand new washer and dryer. brbrSpend the day away enjoying the nearby attractions such as local farm stands, the finest vineyards, breweries, 5 star restaurants located in the town of Southold and Greenport with a 5 minute ferry ride to and from Shelter Island and the famous Sunset Beach.brbrThis property also includes 2 adult kayaks,1 child sized kayak with life jackets and 2 adult mountain bicycles. For the adventurous guest, this is the best location for fishing, boating and jet skiing. Rentals are available merely down the road.brbrLandscaping is also $50 per week
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Exceptional(1)

$385.48

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Private Vacation Home

WALK TO BEACH - Founders Landing, Southold - restaurants, Village, Jitney, LIRR

Southold, New York, United States

BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village - - very short walk to wonderful Bay beach with lifeguard, Walk from jitney and LIRR Southold stop. Delightful setting with exquisite mature gardens, walk to nearby restaurants; North Fork Table, Grateful Deli, Michelangelo's, Southold Social, North Fork Roasters, Juice Bar and Yoga studio, local farm stands, Marina, oyster farm, IGA grocery store, Historic Southold Village Museum.br brVery short drive or bike ride to many vineyards and Long Island Sound beaches, Shelter Island Ferry and a quick 3 mile drive or bike ride to the Maritime Village of Greenport with seaport, many restaurants, and shops. Official Southold rental permit in hand.brbrThis lovely 2 bedroom cottage is furnished with antiques and new comfortable Pottery Barn beds. Air-conditioners, ceiling fans and central heat. New renovated kitchen and bathroom, enclosed porch, and outdoor dining table and chairs, outdoor shower, BBQ Grill. Home has Adirondack chars and fire pit. Hot tub, Kayak, beach chairs and beach cart, kayak, fishing rods and bicycles. Complete with everything needed for a wonderful vacation and romantic beach getaway. Ideal for a couple or young family that loves outdoors: Wonderful bay beach w/ lifeguard just a few blocks down the street. brAvailable May and beyond ( possibly longer ) - two week minimum ( Southold rental permit in hand ) Usually rentals are Saturday to Saturday but there's some flexibility on check-in/out day of the week. We prefer to rent for one month minimum, but flexible. brIf interested, make arrangements to visit ! 201 960 2005
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Exceptional(2)

$923.07

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Private Vacation Home

Privacy!! Heated salt-water pool, central a/c, all kinds of families welcome

Southold, New York, United States

NO BETTER PLACE TO ENJOY THE BEST OF THE NORTH FORKbrDue to the utmost care for your family and mine during the worst of the pandemic, we have not rented for almost three years. Don't let the inaction on the site fool you! brNestled in a giant spruce grove - a Christmas tree farm in the 60's! - this home offers intimate privacy with all the amenities in a spectacular garden setting for a memorable vacation. Airy open plan high-ceiling kitchen-living-dining with wall of windows, skylights, gourmet kitchen with 40 5-burner stove, soapstone counters and farmhouse sink, 3 bedrooms, 3 baths, including full bath on pool level. Central a/c. Spacious two level deck with new gas grill and dining area. High speed internet and cable/Netflix/Amazon/Acorn/Britbox/PBS. Sea kayak on site. Relax by the heated gunnite salt-water pool steps away from the deck, where you can sip a glass of local wine while watching the children play in the specially-constructed shallow splash area of the pool. Or set out for the burgeoning first-class wineries and both sound and bay beaches minutes away. Our local beaches are exceptional for children. Or lie back with the whole family on the sprawling sectional sofa and watch the clouds sail by through the huge skylights. The open living-kitchen area is designed so you can chat with everyone while cooking, eating, watching television, working at the sofa table, or just lounging on the sofa. The extensive fully-fenced, landscaped garden includes flowers for cutting, a full culinary herb garden, and heirloom cherry tomatoes. The circular drive is private, and the house is invisible from the road. The neighborhood has bloomed with organic, farm-fresh, bio-dynamic and u-pick food sources, and several first class vineyards are within 10 minutes of home. We are happy to be able to welcome your family again!
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Exceptional(3)

$472.12

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Private Vacation Home

Surrounded by nature, come stay in this 2 bedroom private, serene location

Southold, New York, United States

Quiet location, surrounded by trees and nature, a pond on the property that brings the beautiful sounds of nature to help relax you in the evening. We are located with a 24 acre persevere behind our home which truly makes you feel a sense of calm. If you are lucky you may spot some deer wandering past your kitchen window in the dawn or dusk, on very rare occasions you may get a glimps of a fox. The various frogs in the pond make you feel as though you are at a nature symphony in the spring & summer evenings. This delightful house features a comfortable queen bed, brand new mattress & bedding. A refreshing new shower with toiletries on hand in the event you forget something. We have a magnified mirror in the bathroom for an added convenience. brbrWe have a new kitchen that includes all you will need, fridge, airfryer/toaster oven, Kurerig as well as a drip coffee machine, microwave, blender, wine opener, induction stovetop.brbrGuests will feel right at home in this soothing retreat, perfect for a relaxing getaway. Book now and enjoy everything this house has to offer. **** This is an apartment with private entrance, technically brand new finished basement with large egress windows in both bedrooms & kitchen bringing in plenty of sunshine**** TWO beautiful Schwinn Bicycles for you to borrow no extra cost as well as a single or double kayak and a paddle board for you to borrow upon request at time of booking. A beach pass is required at all Southold Town beaches, which can be obtained for you for an additional $40. (Town Fee) must be requested 3 days before arrival. I can arrange to have any special requests arranged, such as various favorite foods, snacks, local items from our various farmers markets in season. I am simply a text away always willing to help make your stay as enjoyable as possible. There is brand new washer & dryer for your convenience, detergent will be supplied. brbrThere are 2 quiet adults that live upstairs, you will have complete privacy through your own private entrance away from the main entrance. Security lights illuminate the property as motion is detected. Entrance is around back of house, bluestone walkway will guide you to your private entrance. You will have a private parking area off the street. Feel free to reach out to ask any questions.brbrNearby activitiesbrSwimmingbrWater sportsbrSailingbrWater skiingbrBoatingbrKayakingbrWindsurfingbrWinery toursbrAntiquingbrWildlife viewingbrFishingbrBay/sound
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$965

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Private Vacation Home

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

Southold, New York, United States

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.
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