Home Vacation Rentals By Owner In Montauk, NY

Showing 20 Of 336 Vacation Rentals
Slider Thumb
Exceptional(26)

$719.78

/ Nightly
Private Vacation Home

Beautiful House with Private Beach Access - Rental Registry Cert #23-1,120

Montauk, New York, United States

Create cherished memories in this stunning five-bedroom, three-bathroom beach house in Culloden Shores, Montauk. Designed with families in mind, this spacious and thoughtfully planned retreat offers everything you need for an unforgettable vacation.brbrPrime Location:brbrNestled just steps away from a private beach on the serene Block Island Sound, you’ll love the calm waters, perfect for swimming, paddleboarding, or simply relaxing with your toes in the sand.brbrA short walk takes you to Montauk Harbor, where you can enjoy fishing, shopping, and dining.brbrFamily-Friendly Layout:brbrWith a reverse floor plan, the first floor features four cozy bedrooms, including two with queen beds, one with a full bed, and a kids' room with two sets of bunk beds—ideal for sleepovers and giggles.brbrUpstairs, the expansive open floor plan includes: A modern kitchen with seating for 4. A dining area with seating for 8, perfect for family meals. A spacious living room with a fireplace, a large flat-screen TV, and a pull-out queen sleeper sofa. A second-floor bedroom with a daybed, a bottom trundle, and a dedicated workspace with a desk and printer/scanner for those who need to work remotely.brbrStep out onto the large deck with water views, a BBQ grill, and a patio table—perfect for outdoor dining and sunset watching.brbrAdditional Amenities:brbrWe’ve thought of everything to make your stay stress-free and fun. The house comes fully stocked with: Paddleboards, kayaks, floats, and other water toys for endless fun on the water. Beach chairs, wagons, and towels to make trips to the shore a breeze. A gym in the basement, perfect for weight training and staying active during your stay. A washer and dryer in the basement for your convenience. Kid-friendly amenities (leave your sippy cups and hooded towels at home—just email us for a complete list!). Free WiFi and a large flat-screen TV for movie nights.brbrOutdoor Bliss After a day at the private beach, rinse off in the outdoor shower, surrounded by the beauty of the yard—plenty of space for kids to run and play.brbrEndless Adventures Explore nearby attractions:brbrMontauk Harbor: Just a 15-minute walk away.brbrMontauk Downs Golf Course: A must-play for golf enthusiasts.brbrHither Hills State Park: Enjoy year-round fishing or marvel at the iconic 'walking dunes.'brbrThis home is perfect for multiple families or an extended family vacation, offering the ideal balance of comfort, space, and beachside fun. Just pack your clothing and toiletries, and let the memories begin!brbrBook your dream family vacation in Montauk today!br$1,500 Reservation Deposit required to secure your rental. This Reservation Deposit will transfer to a Security Deposit upon arrival. Security Deposit will be mailed back immediately after cleaning and inspection (within 14 business days) (assuming no damages to the property beyond normal wear and tear).brFinal payment due 5 business days prior to arrival. Payment by Paypal or personal check and NO CASHIERS CHECKS. brbrbrKeywords: beach house, fishing, paddleboard, kayak, family vacation, private beach
Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps

Slider Thumb
Exceptional(15)

$3560.41

/ Nightly
Private Vacation Home

High End Hither Hills Beach House 3 mins to sand

Montauk, New York, United States

*Property is suitable for 8 adults and 5 children max* rental registry #23-1020 REG-14607250brbrA Montauk masterpiece. A Mediterranean inspired oasis 2 mins walk to the beach with and ocean views. This 6 bed 7 bath luxury home is affixed with 3 finished levels, a heated pool and outdoor hot tub, outdoor shower, fire pit area, playground, perfect for grilling meals and has luxury appliances. Two refrigerators, 2 washer/dryers to keep up with this made for families getaway. Smart tv's & Sonos through out the home this solar powered vacation spot allows you to enjoy all the perks with leaving little to no carbon footprint. Home also has an indoor gas fireplace. brbr***For confirmed bookings-you will be contacted a day before or morning of checkin with instructions on how to access the home/schedule a time to meet for keys at the property brbrThings to know before inquiring-brBuild Well has a strict no parties/events policy.brHome is meant for families to rentbrHome has outdoor security camerasbrStrictly no smoking, pets, Bachelor/Bachelorette parties of any kind.brPool is open from Memorial Day Weekend-middle/end of October brHot tub is closed is colder months. Inquire for more details *Please note* we support only a starter supply of toilet paper/paper towels. Extra $50/day for pool heat. Please note, we do not guarantee pool heat is available. If for whatever reason the heater is out of commission we would refund you only for the pool heat fee. Cleaning fee includes hot tub cleaning and garbage p/u. **Please note that when outside temps are under 78 we cannot guarantee that pool will reach desired temp if you choose to pay for pool heat and pool temps can appear lower than they are when outside temps are low. Guests will be contacted the evening before or morning of check in to arrange a time to be Personally checked in between 4-7pm. Please note that during your stay the property may have outside service providers. It’s imperative they be allowed to service the property as this is part of routine maintenance and they may not be turned away.
Bed 6

Bed

Bath 6

Bath

Sleep 13

Sleeps

Slider Thumb
Exceptional(63)

$593.96

/ Nightly
Private Vacation Home

Beautiful Hither Hills Area - Walk to Ocean - Great Off-Season Rates

Montauk, New York, United States

This beautifully decorated home is located on a quiet street in the Hither Hills area of Montauk. It is a 5-minute walk to the ocean, or you may drive and park in the private beach parking lot. The upper level of the house offers an open floor plan which includes the living room with cathedral ceilings, the dining area, gourmet kitchen. The master bedroom and bathroom are located on the upper level as well. Exit the upper level floor through 2 sets of sliding glass doors which open up to a wrap around deck equipped with a gas grill, lounge chairs, and patio dining set. The living room has a gas fireplace and a large flat-screen TV. There are two additional flat-screen TVs located in two of the bedrooms. A retractable awning on the upper deck will keep you cool and comfortable on sunny days as you relax outside listening to the sound of the ocean. The lower level has three spacious bedrooms and a full bathroom. In addition, the house has an outdoor shower, a gas grill, central air-conditioning, and wireless Internet. **Community Public Swimming Pool, Tennis and Golf at Montauk Downs State Park. Horseback riding, biking, fishing, and water sports are all close by.brbrREVIEW NOVEMBER 2020:brEverything about this weekend stay was a 10 plus! The house could not have been more perfect! No details were missed by these great hosts. The furnishing, the appliances and the comfort of all the rooms were perfect! It was a great location for a family dinner and a bucket list dream! Marie Louise was thoughtful and attentive from our first conversation until we checked out. We enjoyed making forever memories! Will definitely be back!br
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(11)

$1660.71

/ Nightly
Private Vacation Home

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

Montauk, New York, United States

Enjoy the kid-friendly heatable pool with retractable safety cover, the adult-friendly hot tub, and bucolic privacy in our lush setting in famous Hither Hills, just a few minutes’ walk to the best ocean beach on Long Island. The 10-sleeper, 3 bed/3 bath upside down traditional Montauk beach house has been dramatically transformed into a spectacular getaway complete with everything you need for a beachside vacation.br brTo start, the new deck dramatically overlooks the backyard pool, lawn, and elegant lounge area, all of which is fully fenced and expansive, perfect for kids (or pets) to romp. Two of the property’s three bedrooms open directly onto the poolside patio, which also contains the 6-person hot tub, so you can wake up each morning to effortless quick dips before hitting the beach or town. A third bedroom has a king bed and ensuite bath. brbrThe large living/dining area supports seating for 12 comfortably in couches and/or soft armchairs and ottomans, so you’ll never resort to the awkward standing or makeshift seating that is all too common in vacation homes (we have not sacrificed comfort for aesthetics). The inside dining table seats 8-10 for family dinners, but you also have two large teak dining tables outside to choose from, 1 on the 2nd story deck just off the main living area and the other at the poolside lounge with the giant firepit, both seating up to 10. brbrThe large pool has a retractable safety cover and is shallow on both sides and deeper in the middle, with stadium steps on both ends, which is great for young kids who can’t venture into deeper water. And yes, an outdoor shower is available, or make that two. One locking and fully private, the other “alfresco” for quick rinses and washdowns after the beach or hot tub. Notably, the property is on town water (not a well), so the pressure is wonderful!brbrThe kitchen has all new appliances, including a convection/induction stove and cooktop, coffeemaker, large microwave, etc. and is directly adjacent to the main living room for easy interaction. The three full baths have two tub/shower combinations and even the auxiliary kitchen “powder room” has a convenient shower. The living room sleeper sofa completes the 10-person sleeping capacity, with the primary three bedrooms having a King, Queen, and two Full beds (bunked). brbrThe living room has a very large Roku TV (also with a cable package) should you need a break from paradise to catch a family movie or sporting event. Two of the three bedrooms also have Roku TVs. Many games and an impressive children’s library will take the edge off any rainy days. The furniture and ambience is all Montauk, both beachy and eclectic, with more than a few historical finds in the mix. brbrSafety is important to us, so you will find multiple fire extinguishers and smoke detectors throughout the property, which is non-smoking. Also, all 1st floor doors leading to the pool/hot tub area are alarmed (to be used at your discretion), in addition to the pool’s electric retractable pool cover. The back yard is completely fenced with child locks on all gates.brbrAttached to the property is a fully separated owner’s cottage that is not included in the rental. Both maintain completely separate keys, entrances, and exits, with no sharing or comingling of any interior or exterior space. Your property is fully private and not shared in any way.brbrA few notes. br-- We are strictly no smoking, of any substance. Weekly professional cleaning is required.br-- Quiet must be maintained after dark (appx. 9pm) to respect the neighbors and tranquility of our neighborhood. Please ensure there are no loud voices, music, machinery, pets, etc. after 9pm.br-- If you have events planned (birthdays, anniversaries, bachelor & bachelorette parties, etc.) you must make this known during your initial inquiry. We may or may not agree to accept your booking based on event details, on a case-by-case basis.br-- Standard utilities are included in the rental price. Propane for heating the pool is not free and is purely discretionary based on individual sensitivities, so if you choose to heat the pool, pro-rated propane charges incurred will be withheld from security. The hot tub is electric heat and always “on”, no propane needed.br-- Pets are allowed but please inquire and alert us in advance to avoid surprises. All pets must stay out of the pool/hot tub and be always monitored to prevent accidents in the lawn, digging, etc.br-- A maximum of three (3) cars are permitted and must be kept in the driveway.br-- We are a no refund property, so please be sure of your plans before booking.br-- Our rental registry is #23-62. We pay Suffolk County Hotel/Motel tax as required by law.brbrPlease reach out with questions or comments and thank you for considering our property!
Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(8)

$1012.68

/ Nightly
Private Vacation Home

4-bedroom Montauk Beach vacation home steps to private beach Dogs/kids welcome!

Montauk, New York, United States

Located in the heart of Montauk is a lovely 4-bedroom getaway. Nestled just a short walk from the private Culloden Shores beach (with lifeguard), this cozy retreat offers the perfect blend of relaxation and adventure. brbrYou'll delight in the property's many amenities, including private beach access, complimentary high-speed WiFi, blackout curtains and a convenient washer and dryer. Enjoy the outdoors with an oversized fenced property with large park-like yard & fire pit. View the Culloden Beach sunset with a picnic and bonfire! Newly renovated kitchen and floors. Sleeps 8 adults in 4 bedrooms + 1 child (fold out futon). 3 outdoor decks w/ separate sitting areas, enclosed shower & BBQ. Walk to Gosmans Fish Market, Tony's Gourmet Meat Market and Deli, Goldberg's Famous Bagels. Many bars/nightlife/live music/restaurants within a 1/2 mile including Bagatelle, Salivars calm and Chowder, Rooted, Lulu's Pizza, Mexican and Seaside Sushi -the best sushi take out in Montauk. brbrVenture out to explore the area's top attractions, such as the captivating Ditch Plains Beach, just a 6-minute drive away, and the iconic Montauk Point Lighthouse, just 12 minutes by car. Back at home, you can savor meals prepared in the fully stocked kitchen, complete with a stove, oven, refrigerator, and more. Gather around the 8+ person dining table or step outside to the deck for a bit of alfresco dining and relaxation.brbrWhether you're seeking a peaceful getaway or an action-packed vacation, our Montauk vacation home has everything you need for an unforgettable stay. Enjoy the convenience of the 4 + car parking, and many entertainment options, including games, books, and toys for the little ones. Immerse yourself in the beauty of the Hamptons and create lasting memories at our charming property. Crib, Pack & Play, bed rails & toddler chair and high chair package available upon request. brbrMin. rental age is 28.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(29)

$904.09

/ Nightly
Private Vacation Home

Hither Hills Ocean Beach House

Montauk, New York, United States

Montauk, at the furthest east end location in Long Island, NY, has the mystique of places at the end of the road. It offers a 'Living End' resort community with a secluded beach, sand and surf, less than 2 short blocks away.brbrOur 4 BR/ 3 Bth Vacation Home is located on a hillside with splendid views of the Atlantic Ocean from its decks. It is nestled among the thick vegetation and oak trees in the Hither Hills area of Montauk, which is known for its charm and serenity.brbrYou can walk to the Ocean beach in under 5 minutes, or else drive down and park in any one of 4 private parking areas on the dunes. We supply all renters with a Parking Permit and Key to unlock gates to these areas.brbrOur home is modern and spacious, and the windows are designed for great natural light and their ability to direct large amounts of fresh wind off the water.brbrA wrap-around Outdoor Deck contains table and chairs, and is shaded under looming pine trees. It lends itself to complete privacy while dining outdoors. The Outdoor Stairs leading to the Sundeck completes the picture with expansive views of ocean and inland. brbrGo to sleep to the lull of the Ocean pounding against the shore, and wake to the rising sun over the water. brbrWhatever you decide, at Montauk ... the wind blows harder, the waves curl higher and the light reflects with a scouring whiteness off the restless back of the Atlantic.brbrKeywords: 4 Bedroom - 3 Bath Hillside Home
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(177)

$942.23

/ Nightly
Cottage

Waterfront Cottage Perfection

Montauk, New York, United States

Perfect Sunsets any time of year —this magical two-bedroom waterfront cottage on bucolic Fort Pond is as close as it gets to perfection. Every room looks out upon the most beautiful waterfront and sunset vistas all year. A designer's home is beautifully decorated with mid-century modern furniture and spectacular landscaping, enhancing the privacy felt on this gem of a property. It features a large living area with ribbon remote control gas fireplace, a dining table, a state-of-the-art kitchen, sofa and a bathroom with a large glass-enclosed rain head shower with access to the outdoor shower from the inside. Ideal for couples, singles, or small families (dogs accepted with a $250 fee, and crated when left alone). Maximum sleeping capacity 4 people. (The sofa should not used for overnight guests and the backs do not go down). The cottage has plenty of outdoor furniture, a table for 8, a gas Weber grill, and stairs to the water—perfect for standup paddleboards or kayaking. A short walk to town (5 minutes), the best restaurants, the Jitney, and beachesbrbrThe cottage comes with linens, towels, beach towels, a fully equipped kitchen, and many beautiful pieces of vintage table settings and glassware for entertaining. (2) standup paddleboards, (2) Kayaks, and (2) bikes. You will be asked to sign a waiver for the use of the equipment.brbrThe cottage is thoroughly cleaned and disinfected between each guest. All surfaces are disinfected with Clorox. All white linens are washed in warm water with bleach. All throw pillows and throws are washable and are cleaned between each guest. brbr$250 per week for cleaning and garbage removal. Excessive garbage will be an additional $75.br$250 Pet Fee per dog, maximum 2 dogs.brNo Cats brbrEast Hampton/Montauk Rental Registry Certificate Number 22-550 (2025)
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(109)

$1091.09

/ Nightly
Private Vacation Home

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Montauk, New York, United States

RR #21-1041 / LIFE SAVING AED DEFIBRILLATOR ON PROPERTYbrbrOUR PROPERTY IS IN PRIME HITHER HILLS WITH PRIVATE OCEAN BEACH ENTRANCES FOR WALKING AND PARKING. YOU CAN WALK TO MONTAUK'S BEST BEACH AND TO TOWNSEND, PLUS GURNEY'S, FROM OUR PROPERTY OR LOUNGE IN THE SALT POOL. BEACH PASS INCLUDED.brbrOUR LARGE PRIVATE OUTDOOR JACUZZI IS OPEN ALL YEAR ROUND; POOL OPEN MAY thru OCTOBERbrbrHighlighting our property -- aside from the quick walk to the ocean beach or town -- is a large, salt-water swimming pool that you can heat if desired, a six person outdoor spa/jacuzzi, and a custom-built, climate controlled, pool house (with sleeper couch for lounging if you need it). All shrouded in glorious privacy. The 20'x40' pool has two shallow ends for enhanced lounging and is a 'sport' design, perfect for volleyball and other pool games.brbrWe are also close to the famous Gurney's Resort, which is walkable in 25 minutes, or just 4 minutes by car. Or take one of our many bikes...brbrHITHER HILLS properties, like this one, come with restricted access to our own beautiful beach below the bluffs along Old Montauk Highway. You get a parking pass for your car to use at the small parking lots at the beach and a key that opens the barrier chain. ONLY HITHER HILLS residents or renters, NOT other homes in Montauk, have this access. Hence the premium prices...and experience!brbrWith that....Our renovated home has 4 bedrooms, 2.5 baths, and 2 great outdoor showers! The private, climate controlled poolhouse has a sleeper couch for lazy poolside lounging when you need it. Ours is a true beach house, not just a house at the beach...and Hither Hills needs no further explanation for those that know and love Montauk; private beach rights on the most beautiful and least crowded sand in the Hamptons. brbrOur home is carefully renovated and furnished throughout with classic white everywhere, replete with beachy antiques and curios we've collected over the years, plus a vast collection of books, many related to the ocean, fishing, and nature. Our home also has two entirely separate living rooms with large flat screens, upstairs and down, so cooking shows on one, sports on the other during rainy days. The half acre property is shrouded in trees on all sides yet has a cozy lawn and a very large and private heated pool, jacuzzi/spa, and air conditioned pool house. A truly luxurious property.brbrThe 4 bedrooms have two queens, one full bunk set, and one twin bunk set, and are nicely spaced across the home's two floors, giving true privacy when you need it. The climate controlled pool house has a pullout sofa for lounging during lazy afternoons in private seclusion.brbrThe home has 6 separate zones (incl all bedrooms) for AC/Heat so you'll never suffer during those hot (or cold) days. The pool house also has it's own separate AC and heat.brbrThe large deck is sun drenched all day and leads to a glorious, large and private outdoor shower. The deck's large round table seats 8-10 comfortably for fresh striper from the grill.brbrAdditional amenities include 2 pull-out sleeper couches for guests (one is in the pool house), second refrigerator/freezer for extra storage, a storage shed with 5 bikes you can use on the many trails around Montauk, plus cable tv, internet, and a wireless networked printer.brbrOur custom, air conditioned, pool house has its own large screen TV (total of 4 on the property), vanity sink, sleeper couch, and plenty of seating so you can cool off during those relaxing days in the pool. The adjacent covered gazebo and large in-ground Jacuzzi can present tough decisions!brbrAnd as our home is in the eastern part of Hither Hills, you can walk to the Surfside Inn (not to be confused with Surf Lodge) for dinner or just drinks...since you won't need to drive home!brbrAlso, we have a child safe home...our 2nd floor deck has locking gates at both stairways and our interior stairway has a permanent locking gate as well.brbrThe walk to the beautiful ocean beach is about 7 minutes and you have a choice of two entrances. Or drive in 1 minute with the provided parking pass.brbrOur kitchen has state-of-the-art appliances, including an induction cooktop for you foodies. New washer/dryer as well. Bedrooms have plenty of hanging and storage space plus additional closets throughout the house.brbrWe take safety seriously so you will find several fire extinguishers and smoke detectors throughout, just in case. Automatic outdoor motion sensor lights provide convenience and safety at night...and tip you off when the deer wander through the yard! We also have an AED (aka Defibrillator) in the home...again, just in case.brbrIMPORTANT: We take pride in the condition and care of our home. While normal wear and tear is expected and anticipated, excessive wear caused by carelessness, overcrowding, or indifference will be noticed and documented on references you will receive from us. Strictly NO SMOKING ON PROPERTY and NO LOUD NOISE OUTSIDE AFTER 9PM in order to maintain the tranquility of our neighborhood.brbrNote: If you have events planned (birthdays, anniversaries, bachelor & bachelorette parties, etc.) you must make this known during your initial inquiry. We may or may not agree to accept your booking based on event details, on a case-by-case basis.brbrWeekly professional cleaning required. Utilities are included in the rental price. Propane for heating the pool is discretionary so usage charges incurred will be withheld from security. Pets may be allowed with additional security on case-by-case basis. Please inquire.brbrThank you for viewing our property and happy vacationing!
Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(21)

$1186.77

/ Nightly
Private Vacation Home

PRICE REDUCED Family Friendly, 3Bd Centrally Located Home with Fenced in Yard

Montauk, New York, United States

Enjoy Montauk for all its pleasures and call this immaculate golf course house your home. Nestled on quiet Fairlawn Drive, you will enjoy a short walk to town, the train station, or the beach. The Manor is just down the street. Take a stroll up to the Fort Hill Cemetery for spectacular sunset views over Fort Pond Bay. If you plan to bring a bike, everything is within biking distance, and plenty is within walking distance. The golf course is just across the street.brbrSet back from the street, this corner lot property holds a quaint 3-bedroom, 1bathroom house with an expansive outdoor shower and private deck. Outside, find a gently sloping lawn with mature trees & landscaping. Fenced in upper yard for your pets. Lounge chairs are in place for you to lie down and relax after a day at the beach, playing on the lake, or out on the golf course. The wrap-around deck is shielded by wooden slats & various plantings, and combined with the patio area & yard, this property offers multiple choices for outdoor enjoyment. There is a gas grill, and newly renovated kitchen with gas range & high end fixtures. You’ll find the extra bar sink in the kitchen especially convenient for hosting family gatherings. brbrCome inside and see the beautiful new renovation. It includes high-end appliances, lighting & fixtures as well as excellently chosen furnishings, and a well-planned layout. Tranquility reigns supreme when you’re inside this light-filled home. Sunlight floods the house all day long with two large sliders and plenty of windows. Cozy up on the couch and lounge around the tastefully decorated living room. The homeowner painstakingly removed all nails and blemishes from a 30-year old deck, and transformed those beautifully weathered boards into dining tables, coffee tables, headboards & more. The kitchen is fully equipped, and the house offers two dining tables suitable for 6, one inside and one outside.brbrThe upgrades continue in the bathroom with brand new fixtures, plenty of storage niches & a pleasing color palate. A full sized washer and dryer are downstairs for your convenience, along with ample space in the full basement to store surfboards, paddle boards, golf clubs, fishing poles, and any other gear you may have. The extra side door allows for easy access. brbrEntertainment includes flat screen TV, generous cable package with tons of movie channels & DVR, WiFi, and wireless speaker.brbrAccommodations include two bedrooms with queen beds, and a third with a double bed. We have a pack n play available should you need to borrow it. We provide all the linens, as well as beach towels. This home is suitable for one or two couples, one or two small families, or one larger family. Briana lives and works locally and is available to answer any questions you may have about the area, or make recommendations on Montauk’s growing restaurant and entertainment scene, as well as the natural resources that everyone loves Montauk for.brbrWell-behaved pets are welcome for a fee, per pet. Maximum total guests: 6brRental Registry # 22-953
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Montauk