Lion Head Beach Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Lion Head Beach

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (74)
"From the minute I stepped on the property and then went inside, I fell in Love! So tranquil and peaceful, yet you can drive 10 minutes into the heart of it all and experience the reasons East Hampton’s is well known for, and then some! I have never been to a vacation home where I didn’t have to scrub down, clean and or have to pack everything I needed because it was ALL there. The attention to every detail .. I thank Rick for that and he was exceptionally responsive! ( this is my first booking...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1030)
"Was visiting family who still live in Montauk. I grew up in Montauk as a kid until i married so very familiar with the area. Loved it then but now its just too, too busy and so many homes and shops, & people. Lots of memories came back even those of watching a movie in the old movie theater & holding an umbrella up over us if it was raining and the cats wandering around brushing up against our legs! Or were they rats??? Lol. The Manor was great though, beautiful and all was perfect! Your...
The price is NZ$769
includes taxes & fees
24 June - 25 June
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (240)
"Access to the beach. "
The price is NZ$670
includes taxes & fees
23 June - 24 June
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (225)
"Very nice location and nice condo"
The Surf Club
Montauk Oceanside Suites
Apartment | Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (306)
"Very good "
The price is NZ$475
includes taxes & fees
24 June - 25 June
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (192)
"Staff is friendly "
The price is NZ$660
includes taxes & fees
23 June - 24 June
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (185)
"Had issue with check in. Nothing sent to phone as stated because of limited cell service in area. Had to go to office to get room and code. They have wrong room and had to go back for correct room. This was frustrating because it was after the check in time, which is later than most properties. The unit was fine, bare bones with decor etc. shower in one bathroom was leaking. I have stayed on property few times. This time was definitely less impressive."
The price is NZ$678
includes taxes & fees
23 June - 24 June
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (12)
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (55)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (26)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (52)
"This restful getaway gave our family a chance to recharge and celebrate family time. The large living space had plenty of room for both hanging out together and for independent chill time. The house had everything we needed for meal prep, and the large kitchen was lovely. The heated pool was our favorite feature. We also walked the paths of the nearby Wildlife Refuge, enjoyed Long Beach, Hamptons Mini Golf, and our favorite dining spots were Boa and the Lobster Roll restaurant. The primary...
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, (13)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (75)
"Ari’s place is a little Alice of heaven! I could sit on the patio all day and listen to the beach across the street. The unit is on the 2nd floor so you can see the waves and any surfers. It’s been thoughtfully renovated and has everything you need. Definitely planning to come back!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.2 out of 10, Wonderful, (29)
"We stayed here for a 3 night weekend getaway for our 10th wedding anniversary. Plenty to explore, pool was open and weather was just gorgeous. Apartment was clean & cute, decor a lil outdated. Only complaint was the queen bed was very uncomfortable and made noise every time you moved."
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
"Salt 'n' Lyme" - Walk to everything !
Exterior
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, (21)
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Newly Renovated Montauk Condo with Ocean Views!
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (64)
"This property was beautiful and Freddy was great. It had everything we needed and will definitely be staying there again. "
Newly Renovated Montauk Condo with Ocean Views!
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Property grounds
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is NZ$11,865
includes taxes & fees
8 July - 9 July
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (92)
"Everything about our stay was 5 star. The host and his wife greeted us, made us immediately comfortable, and were available when we had questions. The house was clean, well kept, and had all the amenities one needs to be comfortable, and the pool, jacuzzi and grounds were spectacular. Proximity to the beach and Montauk town were great, and we lacked for nothing. We definitely plan a return trip! Martha and Peter"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (86)
"It was a cute cottage, nicely decorated. We were very comfortable. Each bedroom had a private bathroom which was very nice. It was close to downtown Southampton so that was great. The owner checked in and was very helpful. "
The price is NZ$1,499
includes taxes & fees
26 June - 27 June
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Montauk Mansion With Outdoor Pool
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
Don't see what you're looking for?
See all available properties in Lion Head Beach
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.

Other types of properties in Lion Head Beach you may be interested in

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (74)
"From the minute I stepped on the property and then went inside, I fell in Love! So tranquil and peaceful, yet you can drive 10 minutes into the heart of it all and experience the reasons East Hampton’s is well known for, and then some! I have never been to a vacation home where I didn’t have to scrub down, clean and or have to pack everything I needed because it was ALL there. The attention to every detail .. I thank Rick for that and he was exceptionally responsive! ( this is my first booking...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (578)
"Love this town and gurneys for decades "
The price is NZ$1,393
includes taxes & fees
23 June - 24 June
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (95)
"After our hotel cancelled on us last minute, we rerouted to the Bentley Hotel. I’m glad we did. Staff were friendly, room was huge and grounds were well maintained. My family had a great Father’s Day weekend at this hotel. "
The price is NZ$484
includes taxes & fees
15 July - 16 July
The Bentley Hotel Southampton
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lion Head Beach holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lion Head Beach. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Lion Head Beach. Seeing all the best attractions is bound to make you fall in love with Lion Head Beach. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Lion Head Beach short-term rentals, that won’t be hard to do.

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?

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: This highly rated holiday home rental in Lion Head Beach is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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

With 19 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 The Hamptons Beaches. In the wider area, you’ll find Amagansett Square and Old Hook Mill.

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.

Recent reviews of Lion Head Beach properties
Expedia verified reviews

Montauk Manor

Montauk Manor

5/5 Excellent
"Was visiting family who still live in Montauk. I grew up in Montauk as a kid until i married so very familiar with the area. Loved it then but now its just too, too busy and so many homes and shops, & people. Lots of memories came back even those of watching a movie in the old movie theater & holding an umbrella up over us if it was raining and the cats wandering around brushing up against our legs! Or were they rats??? Lol. The Manor was great though, beautiful and all was perfect! Your staff were excellent! Thank you!."
A verified traveller stayed at Montauk Manor
Posted 2 days ago
Montauk Manor