The best Airbnbs in Montauk: luxury group rentals at ‘The End’

Neighborhood: Hither Hills

Step inside this sprawling Hither Hills beach house and you’ll find three floors of light-filled space, designed with big groups and multiple families in mind. There are three living areas, a gourmet kitchen, wet bar and multiple outdoor spaces, while the private gunite pool and ocean views bring the holiday-resort feeling. There’s also a personal gym with a Peloton, NordicTrack and weights, plus a five-minute walk to the beach.

Time Out tip: Make the most of the house’s multiple living spaces by splitting up after a beach day. The kids can take over the lower-level entertaining room while everyone else fires up the grill or settles in on the deck.

Sleeps: 10 guests.

Perks: Private pool, ocean views, private beach access, gourmet kitchen, wet bar, personal gym, Peloton, NordicTrack, outdoor shower, EV charger, multiple outdoor spaces, free parking

Price: From $1,368 a night.

Neighborhood: Fort Pond

Perched on a hill behind Fort Pond, this contemporary Montauk home makes the most of its elevated position, with big views across the ocean and Long Island Sound. Built in 2023, the four-bedroom house has an airy open-plan kitchen and living space, a second lounge and plenty of room to spread out across its three levels. Outside, a private gunite pool, lawns and tiered decks provide plenty of spots for lazy afternoons, while the rooftop is made for taking in the scenery. It's also close to popular spots Navy Beach and Duryeas.

Time Out tip: Bring a bottle upstairs at sunset and claim the roof deck. The panoramic views are the kind you’ll want to linger over.

Sleeps: 6 guests.

Perks: Private seasonal heated pool, ocean and lake views, rooftop deck, three outdoor decks, open-plan kitchen, second living room, fast Wi-Fi, free parking

Price: From $1,212 a night.

Neighborhood: Hither Hills

Book this polished Hither Hills retreat and you’ll find a professionally styled, four-bedroom home set on a private wooded acre, with ocean views from the top floor. The open-plan living space and brand-new chef’s kitchen make it well suited to family stays, while an elevator, full-house AV system and multiple outdoor spaces add a touch of hotel-style luxury. Outside, there’s a heated pool, waterfall hot tub and pool house, and the beach is just a five-minute walk away.

Time Out tip: Leave an afternoon free for the pool area. Once you’ve got the hot tub bubbling and the pool heated, you may find little reason to head anywhere else.

Sleeps: 8 guests.

Perks: Ocean views, heated private pool, waterfall hot tub, pool house, chef’s kitchen, elevator, full-house AV system, multiple outdoor spaces, outdoor shower, free parking

Price: From $2,472 a night

Neighborhood: Ditch Plains

Bright, spacious and a little bit fancy without taking itself too seriously, this renovated Montauk beach house is made for laid-back group trips. The reverse-layout home has four bedrooms, five beds and plenty of room for up to 10 guests, with big windows, skylights and cathedral ceilings keeping things light and airy. There’s a professional chef’s kitchen for feeding the whole crew, plus wraparound decking with sunset views, a gas BBQ and an outdoor shower. The beach and Village of Montauk are both less than a mile away, with Ditch Plains Beach around a 15-minute walk. And for an eco-friendly bonus, the 2,500-square-foot home runs entirely on roof-mounted solar panels. 

Time Out tip: The wraparound deck is made for golden hour, so grab something cold, fire up the BBQ and settle in for sunset rather than rushing back into town.

Sleeps: 10 guests.

Perks: Ditch Plains proximity, solar-powered home, chef’s kitchen, wraparound deck, sunset views, outdoor shower, gas BBQ, Sonos sound system, air conditioning, free parking

Price: From $1,711 a night.

Neighborhood: Lake Montauk

This 5,500-square-foot villa is the kind of place where you can bring a very large group without feeling like you’re all on top of each other. The seven-bedroom home sleeps 16-plus guests and sits on a private, fenced acre with views of Lake Montauk. The backyard is the real draw, with a private pool, hot tub, fire pit, hammock and plenty of space for lounging. There’s also a veggie garden, Weber grill and whole-house audio system, while two kayaks and a paddleboard are on hand for trips out on the lake. It’s peaceful and tucked away, but still less than a 10-minute drive from town, the ocean and Montauk Harbor.

Time Out tip: You can really relax here. Paddle out on the lake in the morning, spend the afternoon by the pool and fire up the grill in the evening.

Sleeps: 16+ guests.

Perks: Lake views, private pool, private hot tub, fenced one-acre grounds, fire pit, hammock, veggie garden, two kayaks, stand-up paddleboard, Weber grill, whole-house audio system, beach access, free parking

Price: From $1,945 a night.

Neighborhood: Hither Hills

This bright, modern Hither Hills home has plenty going for it, but the private beach access might just be the biggest plus. Set on more than an acre, the five-bedroom house sleeps 10 and has a 50-foot pool, hot tub and spacious deck for making the most of sunny days. Inside, there are double-height ceilings, skylights and lots of glass, plus a lower-level hangout with a pool table, ping pong and TV lounge. Guests also get keyed access to four private ocean parking lots, meaning getting to the beach is considerably less of a faff than it can be in Montauk.

Time Out tip: Pack the beach towels, grab the parking pass and make a day of Hither Hills beach. Then come home to the pool when the crowds start to thin.

Sleeps: 10 guests.

Perks: Hither Hills location, private beach parking access, 50-foot private pool, hot tub, over an acre of grounds, outdoor deck, pool table, ping pong table, TV lounge, gas and wood grills, free parking

Price: From $2,716 a night.

Neighborhood: Montauk Downs

Golfers, this one’s for you. Set right on the grounds of Montauk Downs Golf Course, this spacious five-bedroom home makes it easy to squeeze in a round before settling into holiday mode. The 11-guest house has a chef’s kitchen, plenty of room to hang out and a heated saltwater pool with a mahogany deck. There’s also an outdoor shower, Sonos sound system, central A/C and two beach cruisers for getting around. And when you’ve had enough of the fairway, you’re still within easy reach of Montauk’s beaches, restaurants and bars.

Time Out tip: Bring the bikes for a spin into town, then come back for a dip in the saltwater pool.

Sleeps: 11 guests.

Perks: Montauk Downs Golf Course location, heated saltwater pool, private backyard, chef’s kitchen, outdoor shower, Sonos sound system, central A/C, two beach cruisers, free parking, beach access

Price: From $3,603 a night.

Neighborhood: near Culloden Point

Set on a peaceful acre just outside town, this elegant four-bedroom home is all about making the most of those Montauk views. Glass doors open onto a wraparound deck overlooking the grounds, with a 30-foot pool, outdoor dining area and plenty of space to soak up the sun. Inside, there’s a generous living room, modern kitchen, four bedrooms and three-and-a-half bathrooms, while ocean beaches and Montauk’s restaurants and shops are just a short drive away.

Time Out tip: Head out for sunset drinks, then come back and make the most of the deck as the water views are the star of the show here.

Sleeps: 8 guests.

Perks: Private pool, water views, wraparound deck, outdoor dining, outdoor shower, spacious kitchen, central A/C, washer/dryer, free parking

Price: From $713 a night.

Neighborhood: Fort Pond

Bright, playful and packed with personality, this retro-inspired three-bedroom cottage puts you within easy walking distance of Montauk’s beaches, restaurants and shops. The newly renovated home has a cheerful, eclectic interior, a fully equipped kitchen and a sunroom for lazy afternoons, while outside there’s a fenced saltwater pool, grassy garden and dining patio made for lingering over dinner. Family-friendly extras include bikes, beach gear, board games and a crib.

Time Out tip: Skip the car when you can. With the beach and downtown both walkable, you can leave it parked and spend the day bouncing between sandy swims, ice creams and Montauk’s bars.

Sleeps: 6 guests.

Perks: Private saltwater pool, walkable to beach and town, fenced backyard, dining patio, BBQ grill, beach essentials, bikes, sunroom, fully equipped kitchen, dedicated workspace, fast Wi-Fi, free parking, pets considered

Price: From $537 a night.

Neighborhood: Downtown Montauk

With the ocean practically on the doorstep, this spacious Montauk home is made for big-group beach breaks. The house sits right in the heart of downtown, with Kirk Park and the sand just steps away via a private beach path, while shops, restaurants and bars are all within walking distance. Inside, there are three bedrooms, six beds and plenty of room to spread out, plus a deck with panoramic ocean views that’s hard to beat for morning coffee or sunset drinks.

Time Out tip: You can leave the car parked for most of the trip here. Spend the day on the beach, wander into town for dinner and come back to the deck when you’re ready to watch the sun go down.

Sleeps: 10 guests.

Perks: Ocean views, private beach access, beachfront location, private beach path, spacious deck, full kitchen, free parking, Wi-Fi, air conditioning, washer and dryer

Price: From $1,912 a night.

Neighborhood: Hither Hills

A 1950s fishing cottage with serious Nancy Meyers energy, Sea Salt Cottage is a beautifully restored little hideaway just a two-minute stroll from Hither Hills Beach. Inside, it’s all carefully considered coastal design, from the open-plan kitchen and heated bathroom to the lofted bedroom and separate artist studio, which doubles as a workspace and reading nook. Outside, a lush garden sets the scene for barbecues, fireside drinks and lazy afternoons in the hammock. Two cruiser bikes, paddleboards, beach chairs and an umbrella are included, too, making it very easy to settle into Montauk’s slower pace.

Time Out tip: Skip the car for a day and take the beach cruisers into Montauk, or walk along the sand and make a morning of it.

Sleeps: 4 guests.

Perks: Steps from Hither Hills Beach; 1950s cottage; private landscaped garden; separate artist studio; outdoor shower; firepit; two bikes and paddleboards; beach gear included; pet-friendly

Price: From $899 a night.

Neighborhood: Ditch Plains

Just a minute from Ditch Plains Beach, this sleek four-bedroom home combines the laid-back pleasures of a beach house with some seriously high-end design. Inside, there’s an open-plan living space, a 12-foot marble kitchen island and a collection of vintage furniture, while outside, two expansive mahogany decks provide plenty of room for long lunches, sunset drinks and post-beach lounging. There’s also an outdoor shower, surfboard storage and six beach cruisers, so getting sandy is very much encouraged. Best of all, the house sits beside a nature preserve, giving it a secluded feel despite being so close to one of Montauk’s best beaches.

Time Out tip: Make a beeline for Ditch Plains in the morning, when the beach is at its best for a surf or swim, then come back for a shower under the stars.

Sleeps: 8 guests.

Perks: One-minute walk to Ditch Plains Beach; designer interiors; chef’s kitchen; two large decks; outdoor shower; private home office; beach cruisers; surfboard storage; parking; pet-friendly

Price: From $1,261 a night.