Vacation Rentals By Owner In Montauk, NY

Have a true Montauk experience in this one-of-a-kind, modern home with three bedrooms, three baths, a heated pool, a hot tub, wrap-around decks, balconies in every bedroom and a designer's personal touch. The living room is bathed in light with ceilings that shoot skyward. The home is the pride of its owners (Because of that, they do not rent to large share groups). Wake up to distant water views and hop to the ocean or bay beaches in mere minutes. Or, just chill by the pool, snooze on a chez lounge or hang about on its ample decks facing North, East or South. Great grill and fully stocked kitchen. The house is ideal for up to six adults. Again, larger adult groups cannot be accommodated.brPANDEMIC ALERT: Availability is contingent on the Covid-19 crisis and local progress toward reopening, but we are reviewing requests as we weigh our renting plan. NOT CONSIDERING REQUESTS FOR FEWER THAN 14 DAYS.brEast Hampton Rental Registry Number: 16-2, 102brKeywords: Modern, barn, construction, wrap-around deck, pool, hot tub, jacuzzi

REAL Montauk w/ pool, hot tub, high design in the heart of Montauk. Pets! View

Montauk, New York, United States

Bed

Bath

6

Sleeps

$1096.56

Although Montauk has changed quite a bit over the years there are still places where you can feel like it hasn't and yet still go into town and enjoy the new Montauk. Green Chimneys is one of those places. Our English-style Tudor house set on 2 acres of land on the golf course will make you feel at home and take you away from all the craziness in town. But if you want to enjoy the beaches, restaurants, bars and cafés in town you are only a mile away. You can easily walk or bike there. The house has 3 double bedrooms and 2 single bedrooms. The two upstairs bedrooms share a bathroom and the downstairs room has its own en suite bathroom. The two single bedrooms are located in the wing and share a bathroom. There is a formal dining room with French doors that lead out to the patio where you can enjoy BBQ's or simply go out to the lawn and bathe in the sun. The living room has a fireplace for those cooler nights when you just feel like hearing the crackling of the fire.

Old World Charm In A New Montauk

Montauk, New York, United States

Bed

Bath

Sleeps

$2083.58

Our architect designed home sits on a gated one acre plot 3 short blocks to a private ocean beach. The property is enclosed by tall trees providing privacy and quiet to make it a perfect family vacation getaway. Amenities include a secluded 40 foot heated pool with blue stone coping, a large irrigated lawn that stays green all summer long, a well that springs water so tasty that we bottle it and bring it back to NYC, and an outdoor shower with a soft rock floor. A master bedroom with changing area and private bath compliments a total of 4 bedrooms plus office/sleep loft. The house sports an upstairs deck off the kitchen that is equipped with an exterior gas grill, and outdoor teak dining furniture with umbrella shade suitable for all meals. The lower patio sits beneath the wood deck as a shaded area for lounging. brbrThe house was designed by architect Roz Young in 1998 and is the quintessential upside down house with an emphasis on privacy from neighbors. All bedrooms are situated downstairs connected by a large mudroom. The master bedroom and master guest both have private door access to exterior spaces, a small deck and patio respectively. The loft is accessible via the upstairs bathroom and looks down on the barn like 1,000 square foot open space, an area prefect for group socializing either by the large plasma tv, around the Housatonic Mills table, or around the carpeted areas for child's play. The house is equipped with high speed wifi internet that reaches the pool and most areas within the property. Premium cable can be accessed in the living room as well as in the master bedroom which also has a large screen plasma. Otherwise, the optimum service allows you to watch your favorite shows on your phone or tablet. brbrThe kitchen is equipped with multiple marble countertops, giving chefs plenty of options for space in which to create delectable concoctions. The open feel is complimented with an island with twin sinks, opposite of which has seating with bar stools for cooking conversation and seating for light meals. The twin door refrigerator dispenses well water and ice. And the kitchen is equipped with a dishwasher.brbrA large laundry machine and dryer is located in the basement. brbrBehind the property, a couple blocks to the north, lies the incredibly beautiful Hither Woods Nature Preserve, a 1,000 acre plus are lush with hiking, biking, and riding trails. When you enter the park, you can bike or walk for hours without coming across anyone else save for wild turkeys, a 25 acre fresh pond suitable for fishing and swimming, and miles of untouched cliffs that run alongside the sound. I often paddleboard with my dog across the pond, taking a path that leads to the sound, and then paddle to Napeague and back, stopping along the way to take in the sights and sounds of the miles of empty shore line.brbr3 short blocks south of the property is the Atlantic Ocean. Parking to access the beach is restricted during daytime hours, so only the nearby community can access the beach. The house has beach chairs should wish to bring them down to the private beach. It's often difficult to tell the difference between off season and high season as the beach is always free of crowds.brbrOur home is far enough from town that you'll never know its busy. And it's close enough to town to enjoy the short 5 minute car ride (or 15 minute jog down the pedestrian only path that leads to town.) Trips to and from town are a highlight in itself along the historic and beautiful Old Montauk highway. brbrFor more on Montauk and the dozens of points of interest from restaurants to the historic light house, to world class surfing beaches, to fabled fishing charters and whale watching, to sunset cocktail spots, please feel free to write to me with your questions. I will NEVER accept wire transfers for your protection. And I will ALWAYS have a conversation with you to confirm your and my identity. brbrReady for adventure in a luxurious setting Check out our recently constructed and posted HA listing: HA 7523167.

Private Custom Built Beach Home with Heated Pool Short Walk to Ocean Beach

Montauk, New York, United States

Bed

Bath

Sleeps

$3556.03

A captivatingly exceptional property, 46 Edison Drive is the epitome of superior quality and modern luxury, enhanced by the unexpected. Superbly placed within Montauk's sought-after Hither Hills, privately sited with ocean views and ocean beach access via Montauk's only private ocean beach association. Tastefully designed by Lukas Machnik, this immaculate turn-key home has beautiful light and superior use of space. There are multiple bedrooms, including two significant privately set Primary bedrooms, each with an exquisite en-suite bath. The upstairs Primary bedroom enjoys a private terrace and private entrance. The downstairs Primary bedroom is complimented by a private sauna and direct entrance to the expansive deck. In addition to the two Primary bedrooms with ensuite baths, there are three upstairs guest bedrooms and two additional baths (one guest bath is ensuite), as well as a third separate windowed room, perhaps a private home office. Completing this floor is a delightful open mezzanine sitting-room/lounge. The first level offers open plan living, dining and kitchen with vaulted ceilings that flow seamlessly to the expansive outdoor deck for elevated entertaining. Also on the main level is a separate and generous family room with wet bar. In addition there is a voluminous separate gym and rec room is also on the main level and can be entered from the main house or via a choice of two private entrances. The custom designed windowed kitchen is a chef's dream and a showpiece, complimented by exquisite cabernet brown marble and stone finishes, Gaggenau appliances, and separate pantry. The lushly landscaped property is enchanting, with room to roam, expansive decking and a sublime newly completed pool with gorgeous custom designed natural stone patio, providing for exceptional outdoor living, relaxation and entertaining. 46 Edison Drive is a truly one of a kind summer home with signature cool and relaxed-chic style.brbrbrOutdoor Furniture: We provide basic outdoor furniture for your personal enjoyment. Please note that the outdoor furniture comes as is and the furniture could be subject to pollen, leaves, sticks and debris from the natural elements. While we will provide best efforts, we are not liable if the condition is not up to your standards. We note that during of winter season, there could be snow: fall there could be leaves: spring and summer, the furniture could experience heavy pollen and/or dusting. We consider this standard for outdoor furniture that is exposed to the elements.brbrYard/deck: We have Weekly lawn service, pool service, and other scheduled outdoor maintenance. Some items to note: We don't know their schedules but assure you when they arrive, the teams work quick and they are very polite. While we have these weekly services, we are not responsible for your dis satisfaction for any natural and organic debris that could fall on the yard between cleanings. These items include, sticks, leaves, pollen or anything else that is considered natural. If you have any questions or concerns, please let us know right away. Please understand that this is nature and some items are out of our control, however, we will do our best to be sure you are happy. Please do not tell any maintenance crews to leave the property. Doing so will cause you to be liable for a displacement fee of $500 and possible loss of occupancy. brbrTrash: The home has weekly trash pick up service. While we have weekly service, we are not responsible if the bin is full between services and consider this ordinary use. Additionally, we are not liable for any inconvenience if the trash is full or odor is strong.brbrBugs and Ants: Please note that the home has a monthly pest control service contract. We consider, ants, insects, ticks and any other natural specimen as ordinary for the country. While we will always make best efforts, we would like to remind guests that mosquitos, ants, bees, and any other pests are a part of the area and not a refection of the homes cleanliness.brbrGrill Use: We provide an outdoor BBQ Grill for your enjoyment. Please note, the grill uses a stand alone propane tank. We do not guarantee that the tanks will be filled, however we will make best efforts. We do have back ups for your ease of use. Additionally, the grill may have food particles stuck to the grill surface. We are not liable for your dis satisfaction and we provide grill tools/cleaning materials if you like to clean the top of the grill.brbrSupplies: The home is maintained very well and we do our best to be sure all necessities are stored in the home. However, if we are missing some items, please let us know and we will do our best efforts to replenish these items. If we are out of paper towels, toilet products, shampoos or anything else you may consider a necessity, we are not liable for your inconvenience and we will not grant any cancellations or discounts as a result of this inconvenience.brbrPool: The pool is open weather dependent and normally from mid may - mid October.brbrCleaners: Our professional cleaners do their best to ensure the house is turned over and clean for the next guests. Sometimes in order to do this if we have guest checking out and checking in the same day, they may go past the 4:00pm check-in time. We ask that you be understanding that this is to ensure a clean environment for your stay and we will not grant discounts as a result of this inconvenience.brbrRepairs: If there is there is any damage or immediate repairs that need to be performed due to any cause ( Act of God, tenant irresponsibility or equipment failure ), the tenant will not be compensated for the disruption. The tenant grant access to the workers in order for the issue to be fixed or resolved.brOther things to notebrbrMost important items, in Summary:br1) Communicate and book in VRBO the exact number of people you intend to sleep at the home.br2) No Parties, No Smoking, No Drugs & please keep a clean and tidy homebr3) Communicate all needs and I will help youbr4) Please respect the home as if it was yoursbr5) No Dinner, lunch of cocktail parties permitted or events. No Drones, large speakers or karaoke machinesbr6) No Loud noisebr7) Receive approval for pets - Pet fee will be incurred.br8) Communication goes a long way w us.br9) No professional services permitted at the homebr10) No Deliveries or packages permitted. (outside of food )brOther things to notebrbr1) No events/parties, No Bachelor or Bachelorette parties or photo shoots. This is a strict policy. Any false statements will terminate your occupancy without a refund and loss of security deposit.brbr2) Please be sure the exact number of people you intend to stay at the home is the exact number of people you booked in the system. Please note, the house has an outside security camera doorbell for house protection. We are reasonable and happy to approval practical requests and encourage you to communicate. Additionally, trying to cover or alter the device will result in immediate termination of the occupancy and no refunds will be granted.brbr3) No entertainment policy. This includes chefs, music coordinators, DJ's, party planners or any other person considered as a hired guest. No Dinner, Lunch, cocktails, showers, events, shoots, or anything that is considered an event w invited guests. The house is meant for your comfort and family / personal enjoyment and not marketed as an event space.brbr4) No Balloons, or signs permitted at the home. No delivery of any items permitted outside of food delivery. No Yoga instructors or Massage therapists. No Photo Shoots or any social media photo shoots, no production movie films. Please: no moving the furniture or beds. No beer pong or similar games. No Diving or rough pool/water play. No Fireworks, Drones or anything that can we launched into the sky. No Karaoke Machines.brbr5) No pets without knowledge and approval. Dogs under 20lbs will be considered and must get prior approval. A minimum non-refundable fee of $200 per pet.brbr6) No Smoking - This is a non-smoking property. There is no smoking inside or outside of the house as well as anywhere on the property. If evidence of smoking, you may be subject to a minimum $500 fine and loss of security deposit.brbr7) Noise - Please observe quiet hours after 9pm. We ask that you be mindful of the neighborhood and if police are summoned due to a noise complaint it may possibly lead to an eviction without a refund.brbr8) Damage & Loss - We would appreciate you treating our home like it was your own. You will be responsible for any damages or loss which will be deducted from your security deposit if warranted. Please advise us of any damage or loss immediately upon discovery.brbr9) Utilities - Utilities are included with this rental and assumed price of $50/day. If Utilities are in excess of $50/day, you may be charged for utilities. Any stay longer than 30 days guest will be responsible for all utilities.brbr10) Early & Late Checkout - Early and late checkouts are available for an additional fee and only permitted if available and on request.brbr11) Renter Age - Primary renter must be at least 30 years of age without prior approvalbrbrRental Contract - The Occupancy Agreement will be agreed to automatically once booked brbrbr

Ocean views, Beach Access, Designer Hither Hills House....

Montauk, New York, United States

Bed

Bath

Sleeps

$1773.78

Montauk offers something for everyone. Pristine beaches with World famous surfing. year round fishing on charter or party boats and surf casting too. Fabulous restaurants, shops and spas right in town. There are hiking trails and the famous Montauk lighthouse. Public tennis and golf within walking distance of house. There are ranches offering horseback riding.brbrThis property is located between Montauk lake and Montauk Downs golf course. It is a few minutes from the harbor, town or ocean beaches.

Luxurious GetAway Home With Lake View

Montauk, New York, United States

Bed

Bath

Sleeps

$506.99

Bring your Surf or Paddle Boards!!!! and walk down your semi-private path (shared with only 4 homes) to one of the most pristine white sandy beaches in Montauk. Imagine not having to deal with Ditch Plains parking! but Beach passes are included to explore other town beach both ocean and bay as permitted. Beautifully decorated it comes with TV and WiFi. Ideal for couples or small family and pet friendly. The property is part of a vintage motel called Twin Pond located on 2.5 acres located at 743 Old Montauk Highway. The studio is open living room and 180 degree views of the ocean (1) queen and sleeper sofa option for a child. It's a short distance to town (you can walk) and is near some of the best restaurant. There is outdoor furniture, a table for 4 and a Weber gas grill. This property is located directly oceanside on the Old Montauk Hwy.brbrWeek begins Friday 4pm and ends the following Friday at 11:00am.brbr$175 cleaning and garbage removal. The dog fee is $250 per dog per week. Only small to medium size dogs. No cats or other animals.

Hotel

Oceanview Chic Alcove Studio, walk to Town/Beach Pass

Montauk, New York, United States

Bed

Bath

Sleeps

$1494.45

This newly renovated house, close to Ditch plains, has 4 bedrooms, 3 full bathrooms, and an outdoor shower. A spacious living room with a loft that has a fold-open futon and a desk. Outdoor entertainment system, new grill, patio furniture, and string lights for ambiance.

Beautiful, spacious, newly renovated house close to Ditch plains

Montauk, New York, United States

Bed

Bath

Sleeps

$1099.66

Amazing ocean views, contemporary great room with soaring ceilings. Beautiful and spacious beach house, with a terrific views of the ocean. The third floor deck wraps around the house, providing a panoramic sight of Montauk's beautiful beach. There are binoculars in the house to allow for whale and dolphin sightings, which happen often at certain times in the day! brbrSet high on a hill, this modern home offers huge views and an open floor plan. Cathedral ceilings, skylights and wrap around glass doors open to an expansive deck that flows seamlessly to the living area and kitchen. Newly renovated and squeaky clean.brbrThere are 4 bedrooms, 2.5 baths, a spacious outdoor shower and plenty of privacy. The house is only short drive or walk to Hither Hills State Park and Gurney's InnbrbrNew A/C in each room, New Privacy shades.

May and June dates available

Montauk, New York, United States

Bed

Bath

Sleeps

$1154.31

Crackling wood fireplace and a cedar sauna set you up warmly for the quiet elegant seasons on the East End, fall & winter. This one of kind Leisurama was re-imagined for its Brooklyn based artist and producer owners. Sexy black framed deck openings, birch ply interior mill work, and a cedar sauna hut and outdoor shower create atmosphere that feels elevated and removed. Surfers are stocked because Ditch Plains is only a 10 minute drive bypassing town. Guests may use the Robert August longboard or Channel Island Pod Mod, easy entry boards. 2 bedroom, 1 queen bed, 2 twin or 1 king, 1.5 bath, outdoor shower, living room sleeper, Aero-mattress, sleeps 6, wood fireplace, outdoor fire pit, grill.

4 Season Design Forward beach house w/ sauna

Montauk, New York, United States

Bed

Bath

6

Sleeps

$667.0

THIS IS A MONTHLY RENTAL ONLY, AS PER THE CONDO BYLAWS.brbrMeticulous, renovated Harbor Ridge condo, situated on secluded cul-de-sac, offers an upside down layout with 2 bedrooms, primary en suite with own deck, guest room with full bathroom on main level. Upper level offers sun-drenched cathedral living area with open kitchen and dining, 1/2 bath, fireplace and 2 sliders to spacious decking with a gas grill and dining table set up. Community pool, central air, gas heat, and lovely pastoral views. brLocated within Montauk Downs State Park, next to a RTJ public golf course. 10 minute bike ride to the beach. It is so quiet and peaceful with plenty of room to relax on the deck or by the pool.brOffered for June, July and or August through Labor day 2026.

Condo

2-bedroom condo in charming Montauk. 10 Minutes to the beach by bike!

Montauk, New York, United States

Bed

Bath

4

Sleeps

$2263.84

Summary:brbrWelcome to Summerlight Estate, a Rove Travel Home!brbrbrbrRove offers beautifully designed residences with the quality and care of a 5-star hotel.brbrbrbrThe Space:brbrEscape to Summerlight Estate, a luxurious villa designed for relaxation and style. This elegant retreat offers spacious living areas filled with natural light, seamless indoor-outdoor flow, and thoughtfully curated furnishings. Step outside to your private pool and sun-soaked outdoor spaces, perfect for lounging, entertaining, or enjoying serene mornings and sunset evenings. Gather around the wood-burning fireplace in the main living area for cozy nights with family or friends. Whether you’re seeking a peaceful escape or a stylish retreat for entertaining, Summerlight Estate combines comfort, sophistication, and timeless design to create the perfect getaway.brbrbrbrPlease note: The pool will be available starting May 20, 2026brbrbrbrTo finalize your reservation, all guests must pass a mandatory third-party screening process.brbr---brbrpbRoom Configuration:/b/pbrbrPrimary Bedroom: 1 king bedbrbrSecond Bedroom: 1 full bedbrbrThird Bedroom: 1 full bedbrbrFourth Bedroom: 2 twin bedsbrbrbrbrpbAmenities:/b/pbrbrpbWork From Home:/b/p High-speed Wi-FibrbrpbLiving:/b/p Fully equipped chef’s kitchen, luxury linens, and premium bath productsbrbrpbSupport:/b/p 5-star service, housekeeping, maintenance, local recommendationsbrbrpbLaundry:/b/p In-unit washer/dryer availablebrbrpbPet policy:/b/p Requires owner approval and are allowed on a case-by-case basis.brbrbrbrpbHome Truths:/b/pbrbrThe pool will be available starting May 20, 2026.brbrbrbrThe pool is serviced and cleaned weekly by a maintenance professional to ensure it remains in excellent condition for guest use, and pool heating is available for $75/day.brbrbrbrOur pool is cleaned and chemically balanced weekly. As an open-air pool, natural debris from wind and breeze are normal between service visits — a skimmer net is available for your convenience. Our team is always happy to assist if needed.brbrbrbrFor safety and proper operation, guests are not permitted to touch or adjust the pool heater equipment.brbrbrbrThe Neighborhood:brbrTree-lined streets and neighboring estates create a peaceful atmosphere, while world-class dining, boutiques, art galleries, and cultural attractions are only minutes away. Iconic ocean beaches are easily accessible, as are local farm stands, tennis clubs, and scenic bike routes. Whether strolling through the village, spending afternoons by the sea, or enjoying sunset dinners nearby, this neighborhood offers the quintessential Southampton lifestyle—refined, relaxed, and effortlessly charming.brbrbrbrOther Things to Note:brbrPets are allowed with owner approval and a one time $350 charge. Rove requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home.brbrbrbrAs a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property. brbrbrbrpbSecurity Deposit Policy:/b/pbrbrA refundable credit card hold of $1,000 is required as a security deposit for stays at this home to cover any property damage that may occur during your stay. A credit card is required for processing and the hold will be placed 48 hours prior to your arrival. The release of this hold will initiate 2 days after your departure following a departure inspection of the home by our local team.

Summerlight Estate by Rove Travel | Villa w/ Pool

Montauk, New York, United States

Bed

Bath

Sleeps

$473.0

Quaint 1 bedroom situated in the heart of Montauk. Walk to town, Navy Beach, or the Surf Lodge. Fully renovated to accommodate 1 - 4 people. Cottage has 1 bedroom, living room with full sized sleeper-sofa, kitchen , bathroom and outdoor patio with ample yard facing the lake. Accommodations includes BBQ, air conditioning, fire pit, 2 kayaks, Bikes ,WiFi & cable TV. Bring surf boards , Bikes, Toys - access to locked storage on property . Centrally located, family-fun is only steps away! We also offer nightly discounts for guest who stay a minimum 7 days or longer .

Cottage

Cozy cottage on Fort Pond Lake.

Montauk, New York, United States

Bed

Bath

4

Sleeps

$1245.17

Montauk tranquility, wake to the birds in this oasis. 3 bedrooms plus sleeping loft, 2 bathrooms on 3/4 acres of paradise. Beautifully appointed personal details abound, chefs kitchen, open floorplan. Outdoorspace abounds. Huge deck off living room on second floor, ground level deck and patio off master bedroom suite. Close to town, ocean beaches and bay. 3 kayaks, 2 bicycles outdoor shower, outdoor bathtub all included.

Sublime Montauk Tranquility

Montauk, New York, United States

Bed

Bath

Sleeps

$1381.48

Perfect for a family or artist getaway, this charming, renovated, 1940-built cottage offers comfort, privacy, and unforgettable ocean views. With two bedrooms and one-and-a-half baths, it comfortably sleeps six. For larger groups, a pull-out sofa in the open concept living room can accommodate two additional guests, bringing the total capacity to eight.brbrCome relax in the indoor heated pool, or soak in the scenery from the spacious ocean-view deck. The renovated cottage is completely private, surrounded by hedges and separated from the rest of the complex—your own hidden retreat.brbrModern conveniences include a newly renovated kitchen with all-new appliances and dishwasher, flat-screen cable TV, Wi-Fi, and even an outdoor shower for post-beach rinses. Best of all, you'll have exclusive access to a private ocean beach just steps away.brbrYou have all the amenities of the Wavecrest Resort, such as Indoor heated pool with lifeguard. Beach boy for lounges and umbrellas. Food truck for excellent breakfasts and lunches. Shuffle Board and outdoor shower on the beach. Most of all a beautiful white sandy beach for Swimming, surfing and exploring for Sea shells and beach glass.brA complete vacation experience awaits your arrival!br“And the Sea, shall bring each man new hope!”brbrPLACES TO EAT IN MONTAUKbrbrDuryea's:brFood served mostly family style & ordered through a counter window (drinks ordered tableside)brLobster cobb salad & market fish are menu highlights (they had a branzino last time I was there and it was TDF) No reservations - on weekends, get there around 5 and expect a wait for large parties unless you want to just do cold seafood inside at the bar (oysters, shrimp, etc.). Grab some rose and wait for your table on the dock. Weekday evenings and lunch are usually a bit slower but the place is generally always busy.brbrScarpetta Beach:brSame as Scarpetta in NYC, traditional Italian food, inside Gurney's hotel.brbrCrows Nest:brSuper chic restaurant at a boutique hotel, one of my favorite places. Mostly Mediterranean inspired, simple menu. No reservations - like Duryeas, on weekends, get there between 5-6 and expect a wait for large parties. They usually cut the waiting list off at a certain point (have waited upwards of 2 hours for dinner here before). Weekday evenings should be more low-key but the closer to the weekend you are the more likely there will be a long wait.brThey have a cute bar down the hill in the bag with a small beach and cabanas set up. Go down and have a drink while you wait for your table and watch the sunset (spicy tequila or watermelon drinks are my favorites).brbrSurf Lodge:brThe quintessential Montauk hotspot. Food is ok, this is more of a place to go to be part of the scene.brOn the weekends this turns into a full-on club - insanely difficult doorman, bottle service, outside DJ (until ~9), sweaty inside bar. Sometimes they have live music on Saturday / Sundays for sunset hours.brbrMontauket:brBEST SUNSET IN MONTAUK. Very casual spot with a divey inside bar and picnic tables outside.brbrGosman's:brCasual seafood spot with a bar - a traditional Montauk staple (not sceney).brNo reservations, so again, expect a wait unless you show up early or during the week.brbrNavy Beach:brBeach front, nautical vibe with lots of white and blue. Food is okay but it's another one of those places sceny NYC people tend to talk about.brI think they take reservations.brbrShowfish:brSeafood restaurant at the other Gurney's property on Star Island. The food is pretty good, traditional. Not really a scene.brI think they take reservationsbrbrJoni's:brGreat little breakfast spot off the main town road.brbrRound Swamp Farm:brMontauk outpost of the East Hampton Farmstand (overpriced but love it)brbrSel Rose:brOysters and cocktails.brbrHarvest On Fort Pond:brOutdoor dining, amazing food.brbrThe Dock:brMontauks best dive bar, super fun, almost tacky vibe, and great food.brbrMontauk Bake Shoppe:brFor jelly croissants.brbrBEACHES & HIKESbrbrGurney's:brThe best beach is the one by Gurneys. The beach is technically public, but they won't let you park on the Gurney's property unless you have a reservation and you won't be able to use their beach chairs. If you want to have a splurge day, rent a cabana or seating area for an afternoon. Sometimes they have a DJ playing on the weekends. Full-service world-class spa on the property.brbrDitch Plains Beach:brMost popular beach for surfing and swimming. Scenic, sort of has a coastal California feel.brbrKirk Park Beach:brClosest to town, family-orientedbrbrHither Hills:brTrails and campgroundsbrbrMontauk Point / Camp Hero:brScenic lighthouse at the end of the road / gift shop with some trails around. Be careful hiking there are tons of ticks.brbrSHOPSbrbrShops in town are mostly of the beachy variety (think Jersey shore hoodies and sweats kind of stuff). In the last ~5 years, they've opened a bunch more stores but mostly womenswear.brbrWhalebone / Adam Mar has some men's stuff I think and there is this new super hip store called wyld blue that is fun to browse.brSome places in town offer surf lessons or paddle board / kayak rentals (you might also be able to book a reservation through Gurney's)brbrDeep Hollow Ranch - horse back riding, etc. - never been here but just saw some brand do an influencer activation and it looked cute.

Cottage

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Montauk, New York, United States

Bed

Bath

Sleeps

$428.44

Located just a short walk to Montauk's pristine beaches ( ocean or bay ), parks, the village, local restaurants and clubs, the train and the Hampton Jitney awaits this small, well appointed space with one bedroom with a separate living and kitchen area. . Nestled in a quiet, old Montauk neighborhood, look no further for a nice relaxing vacation. The cottage ( attached ) has its own separate, private fenced in yard, with a gas grill, outdoor table with umbrella and lounge chairs. We also provide a set of beach chairs and beach towels for your stay.

Apartment

Charming Montauk Getaway centrally located

Montauk, New York, United States

Bed

Bath

Sleeps

$1162.91

This spacious, two bedroom, two bathroom retreat offers breathtaking lakefront views. Designed for relaxation, this property has abundant living space, creating a serene and inviting atmosphere . The property features both an upper and lower deck, each revealing a panoramic view of the shimmering lake and vibrant wildlife (including graceful purple martins soaring overhead). The sounds of nature complement the stunning scenery. From this quiet neighborhood you can enjoy views of downtown Montauk with its lively coastal ambiance just a short distance away. Whether you're sipping morning coffee at sun rise or unwinding at sunset this home is truly a tranquil escape in the heart of nature.

Lakefront two-bed, Approximately 2200 Sq Ft.,two full baths, WiFi and AC

Montauk, New York, United States

Bed

Bath

Sleeps

$2608.71

Get ready to unwind in this stunning 5-bedroom retreat in Montauk where comfort meets costal charm! With spacious accommodations including 1 king bed, 1 queen beds, 1 queen bed 1 sofa bed, and 2 twin beds there's plenty of room for family and friends to relax in style. This home features 3 well appointed bathroom's. Step outside to discover your own private oasis: A gorgeous gunite pool with waterfall, Hot tub and an outdoor shower for that classic beach side experience. Just accross the street your, private beach access awaits. Enjoy 3 levels of Expansive decking ideal for lounging or entertaining while the second and rooftop decking offer breathtaking views of the Long Island Sound & Gardiners Island. Inside the Sun room features a bar & big screen tv creating the ultimate hangout space. Work remotely or just stay connected with fast business wifi a desk. and a printer. With Sunset beach and 10 fantastic restaurants just a shortwalk away at the harbor everything you need is at your fingertips. Your perfect Montauk getaway starts here-reachout anytime during your stay. We're here to make it unforgettable!

Ultimate Montauk Escape ️ 5BR - Heated Pool - HotTub - Rooftop Deck Sunset Views

Montauk, New York, United States

5

Bed

Bath

9

Sleeps

$1281.23

Enjoy your stay at our upside-down style Montauk family home, designed for a peaceful and relaxing getaway with plenty of indoor and outdoor space to unwind.brbrThe home features an inground pool, large outdoor deck, BBQ area, and beautiful sunset views — perfect for summer evenings with family and friends. The open upper-level living space brings in natural light and creates a comfortable atmosphere for relaxing after a day at the beach.brbrConveniently located with easy access to Montauk beaches, town, restaurants, and marinas:brbrBeaches & town: approximately 3.4 miles / 7 minutes by carbrGosman’s Dock & marina area: approximately 0.5–1 mile / 5 minutes by carbrbrThis is our personal family home, not a high-volume rental property. We rent selectively and only a limited number of times each year, primarily to respectful guests and repeat visitors who appreciate the home and the neighborhood.brbrOur property was previously listed on HomeAway for many years before the transition to Vrbo, where we built a strong history of positive guest experiences and repeat stays. Please see reviews in photo sections of listing.brbrWe prefer direct communication with guests whenever possible, so please feel free to message us here with any questions or for additional information about the property and availability.

Montauk Family Home - Pool, Deck, Beaches & Town Nearby

Montauk, New York, United States

Bed

Bath

Sleeps

$1610.93

Secluded, beautiful, pristine beach house getaway in desired Hither Hills. Large 1.7 acre lot with surrounding wetlands allows visitors to escape the mayhem yet .4 mile walk to the beach and 1 mile walk or bike ride to town. brbr3 separate indoor areas for sitting and lounging....brbrMain levelbrSpacious floor plan with cathedral ceilings. Kitchen flowing into living/dining and sun room areas. Stainless steel kitchen appliances, including a Wolf induction oven. Dining area opens to large outdoor deck with a teak dining table which seats 14 and beautiful view. New 2024, 4 burner gas grill.brbrThree beautiful, sun filled bedrooms and two baths. All in pristine condition with master bedroom overlooking pool and hot tub. brbrLower LevelbrLarge walk out lower level provides bright, over-sized second family room where adults or kids can get away to enjoy movies on a 60 flat screen smart TV. Ping Pong and Foosball too! Fourth Bedroom. Full bathroom. Separate laundry room with new washer/dryer, and full bathroom. All in pristine condition. brbrExpansive decks wrapping three sides of the home offering tranquil views from all sides. brbrWonderful location for families and perfect for children. Large lot for running and playing, saltwater pool & hot tub.

Private Beach House on 1.7 Acre in Hither Hills with a .4 mile walk to beach.

Montauk, New York, United States

4

Bed