Lion Head Beach Holiday Rentals

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Holiday Rentals in Lion Head Beach

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
United States
Katie C.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
10.0 out of 10, Exceptional, (90)
"Beautiful house , with pool and amazing backyard, perfect to chill with your friends and family ! "
United States
Priya B.
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1256)
"Beautiful grounds, excellent staff"
United States
Jess
The price is AU$281
includes taxes & fees
3 Nov - 4 Nov
Montauk Manor
Montauk Oceanside Suites
3.0 star property
8.6 out of 10, Excellent, (415)
"We loved it, suite size was great! "
United States
Patrick
The price is AU$256
includes taxes & fees
23 Oct - 24 Oct
Montauk Oceanside Suites
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is AU$460
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (299)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
United States
DongHo
The price is AU$303
includes taxes & fees
21 Oct - 22 Oct
Driftwood Resort
The SandPiper
9.8 out of 10, Exceptional, (27)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
United States
steve
The SandPiper
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
8.8 out of 10, Excellent, (28)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
United States
Allie G.
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (280)
"Very close walk to the beach great for little ones "
United States
Cara Ann
The Surf Club
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is AU$596
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
MONTAUK MANOR-DELUXE STUDIO APARTMENT
9.8 out of 10, Exceptional, (75)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
United States
Katie M.
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Offshore Residences
4.5 star property
The price is AU$1,106
includes taxes & fees
21 Oct - 22 Oct
Offshore Residences
The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AU$257
includes taxes & fees
28 Oct - 29 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
The price is AU$257
includes taxes & fees
22 Oct - 23 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (107)
"Very walkable charming stay in beautiful area that supports larger group. Carter is very responsive and friendly. "
United States
Kendall M.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (76)
"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"
United States
Lisa
Fairy Tale Guest Cottage in Magic Garden by Pool
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,234
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Newly Renovated Montauk Condo with Ocean Views!
9.8 out of 10, Exceptional, (84)
"We had a great time relaxing and taking quiet walks on the beach. The beach access was very close and very quiet. "
United States
Shawn B.
Newly Renovated Montauk Condo with Ocean Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lion Head Beach Hotel Reviews

Find out more about Lion Head Beach

Everything you need to know about Lion Head Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lion Head Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lion Head Beach holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Lion Head Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lion Head Beach. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lion Head Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lion Head Beach holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Lion Head Beach rentals

At Expedia, we put the best Lion Head Beach holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lion Head Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lion Head Beach holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lion Head Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Lion Head Beach?

Yes, there are holiday rentals close to the most popular sights in Lion Head Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Lion Head Beach has to offer?

2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!: This highly rated holiday home rental in Lion Head Beach is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Lion Head Beach?

With 18 Expedia holiday rentals, you're guaranteed to find just the right place for your Lion Head Beach stay.

What’s there to see and do in Lion Head Beach?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like LongHouse Reserve. In the wider area, you’ll find Pollock-Krasner House and Study Center and Amagansett Beach.

What’s a holiday rental in Lion Head Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Lion Head Beach. Holiday rentals feature extras such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.