Holiday rentals in Montauk

4.99 out of 5 average rating, 182 reviews

Duffy's on Lake Montauk 2

These newly renovated units are located on Lake Montauk, five minute drive from town and the ocean beaches. The property offers paddle boards, kayaks and beach chairs. There is a BBQ grill, a fire pit to enjoy sunsets and lounge chairs lake front to relax. The unit has a full kitchen, washer/dryer, queen bed, small living area, large screen TV and wifi. The units sit at a 90 degree angle to the lake with partial lake views from the deck. PRICES INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAX

4.96 out of 5 average rating, 467 reviews

Cabin in The Hamptons

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Guest suite in The Hamptons

4.96 out of 5 average rating, 106 reviews

Twin Pond Ocean View Studio 3

Semi-private path to one of the best beaches in Montauk. Imagine not having to deal with Ditch parking but beach passes included! Twin Pond is a compound on 2.5 acres on Old Montauk Highway. Studio is one of 7 units—galley kitchen (no cooktop) with 180 degree views (1) Qn Size Bed. Walk to Town & restaurants. Modern chic with flat screen TV and WiFi. Ideal for couples/sm family. Outdoor furniture and a gas grill. Dog fee is $150 per dog. Only small to medium size dogs. No cats or other animals.

5 out of 5 average rating, 228 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

4.98 out of 5 average rating, 84 reviews

Beautiful modern retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy getaway. The open-plan interior (wood stove, high-end furnishings/linens/appliances) leads to a covered patio & large yard. (firepit, shower, grill). Beautiful touches everywhere, landscaped for privacy & just a few blocks to LI Sound & Harbor. 3 mi to Ditch Plains or Town. See last photo for accurate location. Note: Owner is in a separate private studio with own entrance. Ask about pet or flexible rental period. 4 people max INCL KIDS.

Holiday home in The Hamptons

4.99 out of 5 average rating, 94 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a short , 3 block walk to one of the most beautiful ocean beaches in the Hampton's! This apartment is located in beautiful, wooded quiet neighborhood. It is a short drive into town where you will find restaurants and shops. This apartment has an open concept living space with a fully equipped kitchen with everything you need ,2 cozy bedrooms and one bath with a walk in shower. We supply beach towels, chairs, umbrella and beach wagon.

5 out of 5 average rating, 29 reviews

Home in The Hamptons

Montauk Village

Remarkable newly built home in Montauk, Winter Sunset View, Walk to Beaches and Restaurants. You will have a stylish experience at one of the most sought after seaside destinations. 3 bedroom, 2 full bathroom and 2 half baths. 9 minute walk to village beaches, restaurants/bars, and shopping In the mood to stay in? Enjoy the hot tub and fire pit. Watch the beautiful Montauk Sunsets "winter is best" from the deck! Central air, internet and wifi

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

4.88 out of 5 average rating, 242 reviews

Cottage in The Hamptons

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

4.9 out of 5 average rating, 465 reviews

Home in The Hamptons

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

4.9 out of 5 average rating, 220 reviews

Montauk Beach Bungalow West

Charming, clean, private, quiet, 2 bed one bath ocean view apartment 500 feet from door to ocean beach through lovely dunes. Dine inside or out with view of the moon rising over the breaking waves. Includes BBQ and fire pit. Full kitchen with stove, oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc. - small bathroom and shower and large outdoor shower

Superhost

4.84 out of 5 average rating, 153 reviews

MONTAUK OCEAN FRONT!

Charming oceanfront Montauk locale with perfect proximity to all town activities! Fall asleep to the lull of ocean waves. Ocean view and steps to the sand and town! New kitchen, Queen bedroom,Queen sofabed in living area, new rain shower bathroom, plus a large front deck for al fresco dining! Perfect for families, and a girls weekend!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Montauk holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Montauk

4.92 out of 5 average rating, 172 reviews

Resort in The Hamptons

Montauk Waterfront Loft Room

CarolynRating, 5 stars4 days ago

Great space! Clean and beautifully decorated. Great neighborhood and stunning views of the water. The pool and area were very well taken care of. Clear and simple instructions. We would stay here again and recommend you book this place!

5 out of 5 average rating, 25 reviews

Sun N Sound Resort, Montauk, NY

RonaldRating, 5 stars4 days ago

Absolutely outstanding stay! The host went above and beyond with exceptional customer service, making us feel truly welcome and cared for from start to finish. Would stay again!

Private room in The Hamptons

4.96 out of 5 average rating, 272 reviews

The Black and White Room.

AdamRating, 5 stars4 months ago

Host is extremely accommodating and considerate. When it snowed he put salt down. Beautiful place with a beautiful fireplace. Peaceful. Host is responsive to all questions. The best stay we had out east and we will return again.

5 out of 5 average rating, 6 reviews

Condo on the Sound - Navy Beach

AshleyRating, 5 stars7 months ago

Tara’s place was a perfect for a weekend getaway! Close enough to town and great view of the sunset!

5 out of 5 average rating, 8 reviews

Home in The Hamptons

New Designer Cottage: Steps To Beach On 1.5 Acres

SarahRating, 5 stars9 months ago

I had the absolute joy of staying at Katie and Robs magical home for a long weekend celebrating my mothers 75th birthday with my sister. What they have created is a true sanctuary! We all felt like we were on retreat. Every detail of their home is thoughtfully done and is just stunning! The bedding was luxurious, and it felt like you were in a home out of a design magazine. It was also in the the most beautiful setting, with an easy walk to a stunning bay, and a short drive to shopping and restaurants. It was truly dreamy!

4.7 out of 5 average rating, 47 reviews

The Exclusive Resort in Montauk

CharlieRating, 5 stars2 months ago

We were very happy with our stay! Great room, cozy and comfortable! The Manor was very nice as well.

4.9 out of 5 average rating, 10 reviews

Oceanfront Corner Studio Bungalow on the beach

EdRating, 5 stars3 weeks ago

Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.