Lion Head Beach holiday homes

We found 1,571 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Lion Head Beach that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, including Wi-Fi and parking. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Lion Head Beach

Showing deals for:27 Nov - 4 Dec

Pool
Living area
Living area
Exterior
Exceptional
(11 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
NZ$20,141
for 7 nights, 1 room
NZ$2,877 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Patio
Private kitchen
Exterior
Dining Room
Exceptional
(99 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

15% off
NZ$14,692
for 7 nights, 1 home
NZ$2,099 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Part of large deck
Kitchen with vaulted ceilings
Dining
Upstairs master bedroom with private bathroom.
Exceptional
(24 reviews)

Huge private 4bdrm, 5 bath, house w/pool. Sleeps 10, near Gurneys! Pet friendly

Montauk

8% off
NZ$14,388
for 7 nights, 1 home
NZ$2,055 per night
includes taxes & fees
Huge private 4bdrm, 5 bath, house w/pool. Sleeps 10, near Gurneys! Pet friendly
Den
Pool
New Kitchen
Living room w/ screen porch beyond
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
NZ$22,463
for 7 nights, 1 home
NZ$3,209 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Covered porch on backside of main house
Pool area viewed from side with teak loungers and umbrellas
Private kitchen
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
NZ$57,165
for 7 nights, 1 home
NZ$8,166 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Living area
Interior
Exterior detail
Exceptional
(10 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
NZ$17,031
for 7 nights, 1 cottage
NZ$2,433 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Outdoor dining
Living area
Living area
Pool
Exceptional
(13 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
NZ$13,311
for 7 nights, 1 home
NZ$1,902 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Living/dining space
Facade
Front yard closeup
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
NZ$9,175
for 7 nights, 1 cottage
NZ$1,311 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Pool
Bedroom #3 Porch
Living Room
Kitchen
Exceptional
(16 reviews)

Perfect Family Retreat With Ocean Views, Heated Pool, And Private Beach Access!

Montauk

12% off
NZ$26,189
for 7 nights, 1 home
NZ$3,741 per night
includes taxes & fees
Perfect Family Retreat With Ocean Views, Heated Pool, And Private Beach Access!
Private kitchen
Pool
Living area
Terrace/patio
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
NZ$27,820
for 7 nights, 1 home
NZ$3,974 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Dining room table - seats 10
Living Room 1
Screened in porch 1
Kitchen 1
Exceptional
(7 reviews)

Retreat to Nature with the best of both worlds - Beaches & Hiking Trails

Montauk

8% off
NZ$21,001
for 7 nights, 1 home
NZ$3,000 per night
includes taxes & fees
Retreat to Nature with the best of both worlds - Beaches & Hiking Trails
Frankel Residence
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Open entry foyer with wall of windowed doors to Zen Garden
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
NZ$27,863
for 7 nights, 1 home
NZ$3,980 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Pool
Living area
Living area
Room
Wonderful
(20 reviews)

Ocean Beach Mini Modern Luxury

Montauk

9% off
NZ$5,236
for 7 nights, 1 home
NZ$748 per night
includes taxes & fees
Ocean Beach Mini Modern Luxury
Guest house small private
outdoor seating area.
Living room, looking out toward Accabonac Harbor, water views.
Bar area pass-through to kitchen, with bar seating.
Lovely seating in pool area for morning coffee.
Exceptional
(7 reviews)

WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!

East Hampton

8% off
NZ$27,031
for 7 nights, 1 home
NZ$3,862 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Interior
Living area
Living area
Dining
Exceptional
(7 reviews)

Modern Home in East Hampton great for a summer or winter retreat.

East Hampton

7% off
NZ$9,403
for 7 nights, 1 home
NZ$1,343 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Second level sunny bedroom with queen bed and views of the pool.
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Living room on main floor with mid-century modern sofa
Exceptional
(18 reviews)

Prime East Hampton Village Location. Heated Pool. Walk To All!

East Hampton

15% off
NZ$13,669
for 7 nights, 1 home
NZ$1,953 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Living area
Private kitchen
Room
Terrace/patio
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

8% off
NZ$9,854
for 7 nights, 1 home
NZ$1,408 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
Dining area
Large pool heated pool
Main living area
Kitchen
Exceptional
(20 reviews)

Charming, spacious 3 bedroom, 3 bath East Hampton Springs house

East Hampton

7% off
NZ$8,725
for 7 nights, 1 home
NZ$1,246 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
NZ$49,998
for 7 nights, 1 home
NZ$7,143 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Primary bedroom with stylish, new, mid-century modern furnishings and pool view
Dine in style overlooking the pool and grounds
New, professional grade, stainless steel appliances including Bertazzoni range
Lounge by the pool in total privacy
Exceptional
(32 reviews)

Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village

East Hampton

15% off
NZ$10,102
for 7 nights, 1 home
NZ$1,443 per night
includes taxes & fees
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
Living area
Terrace/patio
Living area
Interior
Exceptional
(12 reviews)

Large East Hampton house with heated pool and home gym - fully fenced

East Hampton

12% off
NZ$14,626
for 7 nights, 1 home
NZ$2,089 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Interior
Dining
Interior
Main living room and dining room
Exceptional
(28 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

9% off
NZ$22,459
for 7 nights, 1 home
NZ$3,208 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Living Room View#2
Living Room View#1
Shaded Table & Chairs
Sidewalk View #1
Exceptional
(85 reviews)

Whaling Captain Pierson's Cottage

Sag Harbor

8% off
NZ$4,780
for 7 nights, 1 cottage
NZ$683 per night
includes taxes & fees
Whaling Captain Pierson's Cottage
Second eating area
Wrap around deck
Living room
Exterior
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
NZ$12,732
for 7 nights, 1 home
NZ$1,819 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Lion Head Beach getaway

Learn about the unique charm of Lion Head Beach with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Lion Head Beach

Are you hoping to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Lion Head Beach a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • LongHouse Reserve (4.6 mi / 7.3 km)
  • Wolffer Estates Vineyard (8.9 mi / 14.3 km)
  • Kontokosta Winery (11.2 mi / 18 km)
  • Montauk Downs State Park Golf Course (12.4 mi / 20 km)
  • Duck Walk Vineyards (14.2 mi / 22.8 km)
  • Raphael Winery (15.1 mi / 24.3 km)

Exploring the natural features in Lion Head Beach

Whether you're an adventurous traveller or just want to take in the scenery, Lion Head Beach is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • LongHouse Reserve (4.6 mi / 7.3 km)
  • Amagansett Beach (5.8 mi / 9.4 km)
  • Indian Wells Beach (5.9 mi / 9.5 km)
  • East Hampton Main Beach (7.2 mi / 11.6 km)
  • Georgica Beach (8 mi / 12.8 km)
  • Orient Point County Park (8.6 mi / 13.8 km)

Travelling to and around Lion Head Beach

Fly into East Hampton, NY (HTO), the closest airport, located 7 mi (11.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Montauk, NY (MTP), which is 13 mi (20.9 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Lion Head Beach?
Based on our research, houses are considered the most popular holiday property type in Lion Head Beach. But as you know, everyone's idea of an awesome trip isn't the same. Bookabach has holiday homes with every shape, size and budget in mind, so you're sure to discover your ideal match.
How much does it cost to rent a holiday home in Lion Head Beach?
Season, property type and length of stay are some things that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From comfy cottages to sprawling villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Lion Head Beach?
The average price for a holiday home by the beach in Lion Head Beach depends on when you're visiting the area and the size and style of property you're looking for. You can easily find prices on Bookabach by entering your travel dates and destination. Then use our handy filter tool to select the number of bedrooms and amenities that you require, like WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Lion Head Beach?
With 17 properties that welcome four-legged guests, your little buddy can join in the fun on your Lion Head Beach holiday. Use the filter tool to browse our pet-friendly holiday homes and find a stay that's pawfect on Bookabach.
Can I rent a house with a pool in Lion Head Beach?
Grab your swimsuit and swim ring, because there are 14 houses with a private pool in Lion Head Beach. Settle in at one of these superb holiday homes and let every day be a pool day. Simply enter your travel dates into Bookabach, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Lion Head Beach?
A water view, a fireplace and a nearby waterfront top the list of most popular home amenities in Lion Head Beach. Whether you're taking to the road by yourself, with your sweetheart or as a family group, Bookabach can help you find a holiday home that fits your tastes with a load of extras you'll love.
Are there large group holiday homes in Lion Head Beach?
You'll discover three holiday properties in Lion Head Beach that can host 10 or more people. Whether you're planning a trip with extended family or a celebration like a birthday, there's ample room to get your favourite people together under the same roof.
Are there holiday homes in Lion Head Beach that welcome kids?
With 17 family-friendly holiday properties available in Lion Head Beach, there's never been a better time to introduce the kids to the joys of travel. Just click on our "Properties good for families" filter to discover stays that feature conveniences ideal for holidaying families, such as living rooms, outdoor spaces, hot tubs and entertainment areas.
What are the top attractions for families in Lion Head Beach?
There are plenty of fun things to see and do with the family in Lion Head Beach, such as:
  • East Hampton Main Beach
  • Georgica Beach
  • Egypt Beach
Are there holiday homes with WiFi in Lion Head Beach?
Lion Head Beach has eight holiday homes with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to writing and sending emails, these Bookabach homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Lion Head Beach?
Choose from 17 holiday homes with air conditioning in Lion Head Beach giving you that gentle, cool breeze and extra touch of comfort. Just enter your preferred dates of travel and then use our filters to find stays with air conditioning.
How old do you have to be to rent a holiday home in Lion Head Beach?
The minimum required age is usually 16, 18 or 21. It can change between properties on Bookabach, so check the rules of your chosen Lion Head Beach stay before booking your escape.
How long can I rent a holiday home in Lion Head Beach for?
It really depends on the Lion Head Beach property. To view a list of options offering extended stays, simply enter your dates and guest number into the Bookabach search page. Enjoy having the whole property to yourself, along with amenities such as a fully-equipped kitchen and a yard where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.