Top 5 Beachy HomeAway & Vrbo Vacation Rentals In Montauk, Long Island

Top 5 Beachy HomeAway & Vrbo Vacation Rentals In Montauk, Long Island
| 4 min read

Ranked amongst the top places in the USA for having the best wide ocean beaches, Montauk is known for its spectacular 70-foot-high (21-metre-high) bluffs and dramatic unchanged landscapes. With no boardwalks and developments here, it is all natural with low rolling dunes that rim the beach, a guaranteed wholesome experience for anyone who visits.

Located on New York’s Long Island, lounge around the soft fine sand for a tan, or take a dip into azure clear waters. All that’s missing from this carefree and comfortable island lifestyle is a roof on top of your head for you to call home. Well, fret not, for here are the top HomeAway and Vrbo vacation rentals in Montauk, Long Island, to give you the ultimate fun and relaxing beach time:

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on September 12, 2023.

1. Waterfront condo best for families (from 300 USD)

Perfect for your next family vacation, summer getaway, or surfing holiday, this brand-new waterfront condo was created for guests to enjoy the Montauk experience on the shores of Lake Montauk. Thoughtfully designed with wide oak plank floors and a creatively designed wooden shelter, this pretty brick apartment welcomes you in with a wink from the twinkling fairy lights up above. Note that the minimum stay required is two to seven nights. This outdoor / indoor living space clearly gives you the best of both worlds. If nature and the sun aren’t your thing, stay indoors with the comfort of the soft couches and cushions. But don’t regret what you are missing out on! With sufficient shelter and comfy couches for you to laze around, this beautiful outdoor space allows you to enjoy both the beauty and serenity of Montauk. Fall onto the crisp and fresh sheets of this marvellous king-sized bed, or head over to your own private balcony and relax with a drink in hand. This bright and cheery harbour-front master-bedroom terrace is the best place for early morning coffee sips; the view will make you start the day with a smile. The second bedroom is outfitted tastefully with a nautical theme in mind. It features a bunk bed, a 32-inch (81-cm) smart TV, and an en suite bathroom.

Brand New Waterfront - Chic & Sophisticated

Address: Culloden Shores, Montauk, NY (see map)

Price: from 300 USD

Number of Guests: 6

Minimum Stay: 2-7 nights

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2. Refurbished condo with bay views (from USD 329)

This newly renovated condo is just 1.75 miles (2.8 kilometres) from the local beach and 4 miles (6.4 kilometres) from the nearest airport. Decorated tastefully with sea blue couches and seashell paintings, this living room is definitely dressed with an oceanic theme in mind, perfect for beachy Montauk! No fret if you have any unexpected guests, this twin sofa will do just the trick! This very large and fully equipped kitchen features a glass tiled backsplash and granite countertops, as well as all new stainless steel appliances. Enter the calming and serene surroundings of the single bedroom, the brand new queen-sized pillow-top bed a welcoming sight. And, of course, no beach home is complete without an outdoor deck! Feel free to have your meals on the sectional couches as you admire the outstanding views of fort Pond Bay.

Stayed at this property?
Montauk, New York, United States
condo 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
pool is a bit from the room but the views are amazing
from a fully stocked kitchen to a cozy and comfortable bedroom/living room
we didn't use the kitchen but it was well stocked with everything
everything was clean new and comfortable
the condo itself was beautiful and very clean
we really enjoyed staying here the place was just as pictured - clean with great views
owner is wonderfully responsive to q&a
beautiful sunsets and good host
the location was easily accessible to a few different beaches and all of the best restaurants in montauk
but the first night viewed the beautiful sunset that can be enjoyed by visitors at this location
great stay right by the bay with calm waters and a rocky beach
very clean and cozy place located on the beach with amazing sunset views
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3. Charming cottage with ocean views (from 250 USD)

This charming vintage-style Montauk beach cottage suits both families and couples. It is a great location at Old Montauk Highway, which means a fast walk to one of the best beaches in Montauk. Enter the charming and spacious living room, proudly furnished with wooden-planked walls and floors. Check out the cute country flags and the various framed pictures; this apartment was clearly decorated with a rustic and homely feel in mind. Snuggle up with a cup of hot chocolate in hand, this toasty fire will be sure to keep you warm. Doesn’t this look like a set from Tarzan? Laze on the cosy single bed in the sun room, or relish the stunning ocean view from the large glass windows. This 2-twin bedroom sure does give off a comforting and homely vibe. Rest those tired eyes and legs of yours in this cosy spot, the best end to a tiring day. There are two outdoor decks in this lovely home, so do not hesitate to embrace nature in all of its beauty.

Beautiful Montauk Ocean View Beach Cottage

Address: Near Madison Drive, Montauk, NY (see map)

Price: from 250 USD

Number of Guests: 6

Minimum Stay: 2 nights

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4. Cozy resort condo with beach access (from USD 293)

This luxury condominium resort is located on the most beautiful stretch of Ocean Beach in the Hamptons, a two-minute walk from the charming village of Montauk. Feast your eyes on restaurants, shops, and bicycle rental. Relaxation, sun, ocean surf, and luxury surroundings are yours for the asking. The living room has a comfortable sofa, which pulls out to a queen-sized bed. Air-conditioning is provided for complete comfort. A lounge chair, ample closet and storage space, a flat-screen colour TV with cable channels, HBO, DVD player, clock radio, and a telephone with a message service are also available for use. Relax after a lovely beach day in this comfortable master bedroom with a queen-sized bed. The master bedroom also includes a sink / vanity, for you to do any last-minute make-up touch ups. The ocean is calling! Be careful not to miss a step as you zoom down this stairway to the ocean and beach at the Surf Club. A spring in your step, a smile on your face, skip down this walkway to the Surf Club. You’re almost there! Ta-dah! Be mesmerised by the crashing waves and the soft blue sky, and soak in the beauty and splendour that Montauk has to offer.

Stayed at this property?
76 reviews   Wifi Available
condo 4 Guests 1 Bedroom 2 Bathrooms

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the condo was very clean and comfortable with all the amenities you need
the pool is gorgeous or you can get an umbrella and chairs to hang out at the beach
the unit is clean and well kept
the place was clean and the location had a view of the pool
the surf club staff was wonderful
the staff was amazing and so helpful
the owner is so sweet and so nice
the owner always responded quickly and checked in before going to make sure we were all set
the owner immediately contacted me about the booking and providing a lot of useful information
great restaurants lobster rolls frozen yogurt are within walking distance
great location right on the ocean and really great pool on the property
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Oceanfront condo with pool access (from 264 USD)

Located directly across the Old Montauk Highway from beautiful Montauk Beach, this newly updated condo is only a 3-minute walk from the beach and a 10-minute walk from downtown Montauk. The living room also serves as a bedroom that can fit two adults comfortably, as each side of the couches is the size of a twin mattress. The bedroom now includes an all-new queen-sized luxury pillow-top mattress and and thick fresh comforters to always keep you warm. Head out to your own private balcony and admire the spectacular views of the beach and ocean. Relish the sights that only Montauk can offer! The beach is awesome, but the community pool is not too bad either. Take a short stroll to the community pool and dive in, something you can’t do from the shores of the ocean.

Newly Renovated 1 Bedroom/ 1 Bathroom Montauk Oceanfront Condo

Area: Old Montauk HWY, Montauk, NY

Price: from 264 USD

Number of Guests: 4

Minimum Stay: 2-7 nights

Stayed at this property?

The ocean is calling

Splash in the never-ending azure waters. Soak your toes into the fine soft sand. Admire the seashells that line the golden beaches. If you don’t mind the fine sand stuck in between your nails, your tan will eventually start to glow. Montauk is definitely an ideal place for beach lovers. Crash into paradise and be at one with the waves and, hopefully, be at one with our recommended beach HomeAway and Vrbo vacation rentals too!

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Clara likes to spend her time daydreaming about countries she has never visited before, and while she is at it, exploring new cafes and cool spots in Singapore. She is passionate about reading and...Read more

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