Lion Head Beach holiday rentals

We found 1,574 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:13 Nov - 20 Nov

Exterior
Living area
Pool
Dining
Exceptional
(10 reviews)

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

Orient

8% off
AU$16,975
for 7 nights, 1 room
AU$2,425 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Dining Room
Private kitchen
The Harbor
Exterior
Exceptional
(97 reviews)

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

Sag Harbor

16% off
AU$11,901
for 7 nights, 1 home
AU$1,700 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Pool
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
AU$11,651
for 7 nights, 1 home
AU$1,664 per night
includes taxes & fees
Huge private 4bdrm, 5 bath, house w/pool. Sleeps 10, near Gurneys! Pet friendly
Private kitchen
Pool
Terrace/patio
Living area
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,327
for 7 nights, 1 home
AU$3,332 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Pool area viewed from side with teak loungers and umbrellas
Covered porch on backside of main house
Main house living room
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
AU$48,146
for 7 nights, 1 home
AU$6,878 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Bedroom #3 Porch
Kitchen
Living Room
Exceptional
(16 reviews)

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

Montauk

12% off
AU$21,969
for 7 nights, 1 home
AU$3,138 per night
includes taxes & fees
Perfect Family Retreat With Ocean Views, Heated Pool, And Private Beach Access!
Frankel Residence
Thermador chefs kitchen with expansive island open to dining room & family room
View from entry foyer into double height living room, skylights, leading to pool
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Exceptional
(6 reviews)

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

Wainscott

8% off
AU$23,363
for 7 nights, 1 home
AU$3,338 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living room w/ screen porch beyond
Pool
Den
New Kitchen
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,890
for 7 nights, 1 home
AU$2,699 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Living area
Pool
Interior
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
AU$20,647
for 7 nights, 1 cottage
AU$2,950 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Living area
Terrace/patio
Living area
Interior
Exceptional
(11 reviews)

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

East Hampton

12% off
AU$17,815
for 7 nights, 1 home
AU$2,545 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
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
AU$22,669
for 7 nights, 1 home
AU$3,238 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
living area with gas fire leads onto the deck
huge swimming pool and deck surrounded by trees
kitchen backs onto the garden
kitchen leading into open plan living area
Exceptional
(53 reviews)

Large heated pool, games room, private bay beach access, gardens, kid-friendly

East Hampton

8% off
AU$7,206
for 7 nights, 1 home
AU$1,029 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
From the bedroom
Facade
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Living/dining space
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,608
for 7 nights, 1 cottage
AU$1,087 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Interior
Dining
Main living room and dining room
Night time at the pool
Exceptional
(28 reviews)

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

Sag Harbor

8% off
AU$20,544
for 7 nights, 1 home
AU$2,935 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Living area
Dining
Outdoor dining
Pool
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
AU$42,065
for 7 nights, 1 home
AU$6,009 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Kitchen 1
Living Room 1
Dining room table - seats 10
Screened in Porch 2
Exceptional
(7 reviews)

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

Montauk

8% off
AU$17,685
for 7 nights, 1 home
AU$2,526 per night
includes taxes & fees
Retreat to Nature with the best of both worlds - Beaches & Hiking Trails
Exterior
Large pool heated pool
Kitchen
Dining area
Exceptional
(20 reviews)

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

East Hampton

7% off
AU$7,294
for 7 nights, 1 home
AU$1,042 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Dining
Property grounds
Interior
Living area
Exceptional
(95 reviews)

Private and Immaculate East Hampton Home With Heated Pool

East Hampton

8% off
AU$6,562
for 7 nights, 1 home
AU$937 per night
includes taxes & fees
Private and Immaculate East Hampton Home With Heated Pool
Three Mile Harbor, glorious sunsets, and waterfront restaurants- 8 minute drive
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Living room on main floor with mid-century modern sofa
Second level sunny bedroom with queen bed and views of the pool.
Exceptional
(18 reviews)

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

East Hampton

15% off
AU$10,453
for 7 nights, 1 home
AU$1,493 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Pool
Interior
Living area
Exterior
Exceptional
(10 reviews)

Lovely Private Estate In East Hampton

East Hampton

8% off
AU$7,046
for 7 nights, 1 home
AU$1,007 per night
includes taxes & fees
Lovely Private Estate In East Hampton
Bright living room with stylish, mid-century modern furnishings
Swim in the solar heated pool or basque in the sun...
Spacious, stylish, and bright dining room
Sunlit living room with wide sliding glass doors that lead out to sundeck.
Exceptional
(10 reviews)

Walk to Village, Bike to Ocean, Relax in Solar Heated Pool

East Hampton

15% off
AU$8,330
for 7 nights, 1 home
AU$1,190 per night
includes taxes & fees
Walk to Village, Bike to Ocean, Relax in Solar Heated Pool
Interior
Living area
Living area
Room
Exceptional
(7 reviews)

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

East Hampton

7% off
AU$7,801
for 7 nights, 1 home
AU$1,114 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Room
Living area
Pool
Living area
Wonderful
(18 reviews)

Ocean Beach Mini Modern Luxury

Montauk

9% off
AU$4,318
for 7 nights, 1 home
AU$617 per night
includes taxes & fees
Ocean Beach Mini Modern Luxury
Room
Private kitchen
Terrace/patio
Living area
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

8% off
AU$8,178
for 7 nights, 1 home
AU$1,168 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
  • 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)
  • Duck Walk Vineyards (14.2 mi / 22.8 km)
  • Raphael Winery (15.1 mi / 24.3 km)
  • Pindar Vineyards (15.3 mi / 24.7 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 best area to stay in Lion Head Beach when booking a holiday rental?
When considering a holiday rental in Lion Head Beach, New York, a popular area to stay is in the vicinity of the beach itself. This lovely neighbourhood is ideal for those who appreciate the soothing sounds of the waves and the convenience of being close to the shore. Here, you can find a variety of properties, ranging from charming cottages to modern homes, allowing you to choose something that fits your preferences and budget.The nearby beach is the main attraction, offering ample opportunities for sunbathing, swimming, and beachcombing. Additionally, the scenic walking trails and parks in the area provide a superb backdrop for outdoor enthusiasts. Another point of interest is the local dining scene, where you can enjoy fresh seafood and other culinary delights.
What are the top attractions in Lion Head Beach?
In Lion Head Beach, visitors can enjoy a tranquil atmosphere with a focus on outdoor activities. The beach itself is a prominent attraction, offering scenic views of Lake Ontario and opportunities for swimming, sunbathing, and picnicking. The area is ideal for nature lovers, with nearby hiking trails that provide access to the stunning landscapes and wildlife of the surrounding region.The charming local community often hosts seasonal events, such as farmers' markets and arts and crafts fairs, which showcase the area's local produce and crafts. Additionally, the nearby parks and nature reserves, such as the scenic Lakefront Park, offer further opportunities for outdoor recreation, including walking paths and picnic areas.
Are all fees included in the Lion Head Beach holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Lion Head Beach holiday homes with parking?
Stayz offers a wide selection of holiday homes in Lion Head Beach with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Lion Head Beach holiday homes?
You can find great discounts on holiday homes in Lion Head Beach on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Lion Head Beach holiday home booking on Stayz?
To find Lion Head Beach holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Lion Head Beach?
A long-stay holiday home in Lion Head Beach is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Lion Head Beach holiday home?
Book your Lion Head Beach holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Lion Head Beach?
Prices for holiday homes in Lion Head Beach vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Lion Head Beach to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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