50 Best Long Island Apartments on Holiday Lettings - Condos

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369 Vacation rentals

17

Cottage rental in Long Island

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6,000 / week

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from $900 / night

15

East Marion Vacation home rental

North Fork / East Marion

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Renovated Waterfront Cottage with private beach and spectacular views! The house sits on the edge of the bluff with views of a secluded cove on the sound and has access to an infinity deck where you can relax and enjoy the water views, the sunsets, the landscaped garden …see more

from $470 / night

$3,290 / week

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from $470 / night

21

Long Island Vacation cottage rental

Fire Island / Fair Harbor

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
An ideal spot for a comfortable, peaceful beach vacation. Our charming, renovated cottage is located in Lonelyville, on Fire Island a short drive or train ride from New York City. If you've never visited Fire Island you're in for a treat. Close to the city yet a galaxy …see more

from $850 / night

$5,000 / week

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from $850 / night

20

Vacation home in Long Island

Hamptons / Southampton

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1,661 / night

$11,627 / week

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avg. 3 hours 8 minutes

from $1,661 / night

11

Vacation home in Long Island

Hamptons / East Hampton

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A new construction estate in the exclusive Georgica Pond section of East Hampton brings the fabled tradition of Long Island country houses into the here and now. This gracefully proportioned gambrel home continues the proud lineage of East Hampton estates for the New co …see more

from $5,715 / night

$40,000 / week

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avg. 17 minutes

from $5,715 / night

8

Villa rental in Long Island

Long Island / Bayville

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
This is a luxury, modern, waterfront house with 4500 square ft. There are 10 large rooms. All rooms have wall to wall glass windows overlooking the bay. Brand new house with all brand new appliances. KItchen, 2 living areas, 2 fire place 2, dining room, family room, rec …see more

from $950 / night

$6,650 / week

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from $950 / night

13

Vacation home in Long Island

Hamptons / East Hampton

5 12 30 nights min

  • 5 bedrooms
  • Sleeps 12
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Furnished 5 bedroom 4 bathroom home on a quiet cul de sac. In-law/nanny suite with private bathroom and living room. Viking/subzero appliances with granite countertops. Spacious deck and Porch on one acre piece of property. Great house for entertaining. Air conditioning …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

19

Home rental in Long Island

Fire Island / Ocean Beach

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This home is in a unique summer beach community on fire island in New York. The area is accessible by passenger ferry or boat. Motor vehicles are not permitted. This lovely home is a short stroll to the ocean beach. It is close to all local amenities, such as restaur …see more

from $800 / night

$5,600 / week

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from $800 / night

18

Vacation cottage in Long Island

Hamptons / Montauk

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Pet friendly
Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to priv …see more

from $334 / night

$2,334 / week

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from $334 / night

21

Home rental in East Hampton

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Green Rock is located in the Northwest Wood section of East Hampton. The property is so well situated you will probably not want to leave it. The moon rises over the water, the sun sets in the back. Turn on the landscape lighting, open a great bottle of wine and enjoy …see more

from $900 / night

$6,300 / week

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from $900 / night

14

Long Island Vacation cottage rental

Long Island / Fire Island

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitted on …see more

from $658 / night

$4,600 / week

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from $658 / night

(9) Excellent 

18

Vacation cottage in Cutchogue

North Fork / Cutchogue

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fi …see more

from $150 / night

$950 - $2,030 / week

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from $150 / night

24

Vacation home rental

Long Island / Fire Island

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
Discover the hidden treasures of Fire Island from this 4-bedroom, 2-bathroom vacation rental house with sleeping accommodations for 10. The property boasts 2,200 square feet of living space, an expansive mahogany deck and breathtaking views of the Great South Bay. Only …see more

from $500 / night

$3,500 - $7,000 / week

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avg. 14 minutes

from $500 / night

(3) Excellent 

19

Vacation home in Long Island

Long Island / Westhampton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the bay side of Dune Road on a scenic peninsula and surrounded by water, this contemporary is a beach lovers paradise. It's a short walk to the great Westhampton Beach, one of the top 15 ocean beaches in the country; a 5 minute drive to the village; or you ca …see more

from $190 / night

$975 - $3,500 / week

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from $190 / night

11

Home rental in East Quogue

Hamptons / East Quogue

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This 4 bedroom, 2 bathroom contemporary is just steps away from a private beach and marina. Some amenities include: New granite kitchen Cathedral great room with flat screen tv Hardwood floors Multi level decking In ground heated pool Patio furnitur …see more

from $500 / night

$3,500 / week

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from $500 / night

(3) Excellent 

11

East Marion Vacation cottage rental

North Fork / East Marion

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to the Victorian Seasons guest cottages, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful Nort …see more

from $400 / night

$2,600 / week

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from $400 / night

(3) Excellent 

17

Home rental in Long Island with tennis court

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Will your mom have to sit on the end of your futon with a plate of holiday goose and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the roast she bought doesn't fit in your oven? Well it is time to …see more

from $400 / night

$1,500 / week

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from $400 / night

24

Home rental in Greenport

North Fork / Greenport

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical town of Greenport, this home provides a unique New York experience, sans big buildings and bustling sidewalks …see more

from $260 / night

$1,820 - $2,450 / week

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avg. 13 minutes

from $260 / night

(1) Excellent 

23

Long Island Vacation home rental

Fire Island / Cherry Grove

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
THE MOST DESIRABLE LOCATION IN CHERRY GROVE. ONLY 1 SUMMER WEEK LEFT! Come join us in our fabulous get-a-way from the hustle and bustle of everyday life. This incredible "gay" oceanfront property is nestled in Cherry Grove, Long Island which hosts beautiful white sandy …see more

from $400 / night

$3,200 - $6,000 / week

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Responds fast!
avg. 3 hours 44 minutes

from $400 / night

15

Vacation cottage in Long Island

Long Island / Baiting Hollow

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants. …see more

from $150 / night

$800 / week

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from $150 / night

(9) Excellent 

28

Vacation home in Long Island

Southampton / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room o …see more

from $400 / night

$3,000 / week

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Responds fast!
avg. 2 hours 44 minutes

from $400 / night

17

Vacation home in Greenport

North Fork / Greenport

4 11 2 nights min

  • 4 bedrooms
  • Sleeps 11
  • 2 nights min
1903 Village Farmhouse, full of character, light and air. A place to relax, unwind and drink wine on the front porch, say hello to our neighbors or take an afternoon nap. Walk into the village for shopping and dinner or ride your bike to the beach. Visit one of the m …see more

from $400 / night

$3,000 - $5,000 / week

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from $400 / night

(1) Excellent 

10

Vacation cottage in East Marion

North Fork / East Marion

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
. North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Itali …see more

from $400 / night

$2,200 / week

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from $400 / night

11

Vacation home in Long Island

Hamptons / Westhampton

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
This 3 bedroom, 2 bath ranch house is in excellent condition and is newly furnished for comfort, style, and flexibility. Sitting on 1.5 acres the house is very secluded and private and just a short drive to West Hampton Beach and many beautiful beaches and parks. There …see more

from $450 / night

$2,800 / week

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from $450 / night

(14) Excellent 

24

Long Island Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Minimum two-week stay. This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close …see more

from $358 / night

$2,500 - $5,000 / week

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Responds fast!
avg. 3 hours 36 minutes

from $358 / night

34

Apartment rental in Long Island

Southampton / Hampton Bays

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Ask about children
WaterFront Walkout is the Ground Floor of Stunning Private Legal 2 Family with 1500 Sq. Feet, Roomy Open Floor Plan, Laundry Room, AC, Heat & Water Views Galore. The Upper Unit is never Rented and for Owner's Exclusive Use Only. It is Available For Short Stays Year Ro …see more

from $350 / night

$2,500 - $3,900 / week

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from $350 / night

(2) Excellent 

7

Vacation home in Long Island

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated d …see more

from $370 / night

$2,600 - $5,900 / week

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from $370 / night

(1) Excellent 

21

Vacation home in East Marion

North Fork / East Marion

1 3 90 nights min

  • 1 bedroom
  • Sleeps 3
  • 90 nights min
  • Child friendly
  • Air conditioning
This is a one-bedroom efficiency apartment with a kitchen and bistro dining area, located in the heart of East Marion on the beautiful North Fork. It is part of the main farmhouse that dates to the late 1800's with a separate entrance that once belonged to the Stars fa …see more

from $180 / night

$1,100 / week

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Responds fast!
avg. 1 hour 54 minutes

from $180 / night

31

Vacation home in Long Island

Long Island / Lido Beach

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Magnificent Ocean Front Contemporary Beach House!! Open & Inviting floor plan with hardwood floors thru out! Gourmet Kitchen, Living Room, Dining Room, Den/Family Room, 3 Bedrooms, 3.5 Baths, Handicap access with elevator and ramp. Roof Top Deck, garage,driveway, patio …see more

from $1,200 / night

$8,400 / week

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from $1,200 / night

27

Long Island Vacation apartment rental

Long Island / East Patchogue

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
  • Private garden
Gorgeous 2nd Floor Private entrance apartment with its own deck over looking the Great South Bay - Large bedroom - Bath & Living spaces , Kitchen w/washer dryer. All emendates, central heat & ac- w/internet , direct tv , private parking on 5 acres estate, 10 min to Vil …see more

from $145 / night

$950 / week

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from $145 / night

(7) Excellent 

30

Vacation home in Kismet

Fire Island / Kismet

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Our wonderful cottage comes with all the expected amenities for the total vacation experience. It has two decks, a large private rear deck and fun smaller front deck for people watchers . Fire Island boasts no private cars in the summer until Sept 15 so the kids have fr …see more

from $325 / night

$2,000 - $3,500 / week

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Responds fast!
avg. 3 hours 50 minutes

from $325 / night

(2) Excellent 

17

Vacation home rental

North Fork / Southold

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, …see more

from $375 / night

$2,500 / week

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from $375 / night

25

Home rental in Greenport

North Fork / Greenport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a …see more

from $300 / night

$3,000 - $5,000 / week

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Responds fast!
avg. 3 hours 43 minutes

from $300 / night

21

Vacation home with swimming pool, golf nearby in Long Island

Long Island / Bellport

3 10 4 nights min

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer …see more

from $400 / night

$3,000 / week

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from $400 / night

(5) Excellent 

14

Home rental in East Marion

North Fork / East Marion

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, …see more

from $249 / night

$1,500 - $2,900 / week

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from $249 / night

23

Vacation home in Long Island

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cath …see more

from $1,200 / night

$8,000 / week

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Responds fast!
avg. 3 hours 41 minutes

from $1,200 / night

(8) Very Good 

11

Vacation b&b in Long Island

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Car not necessary
This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. One bedroom has a water view, the second bedroom is larger at the front of the house, and they share a dressing room/office. …see more

from $500 / night

$3,500 / week

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from $500 / night

33

Apartment rental in Ocean Beach

Fire Island / Ocean Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary
Ocean Beach, Fire Island, NY Summer Rental. Steps from beautiful ocean beaches, shops, restaurants, night life, ferries and all the Capital City of Fire Island has to offer. Credit Cards and Pay Pal Accepted. MINIMUM RENTAL 3 NIGHTS. See Photo inlay …see more

from $250 / night

$1,200 - $3,300 / week

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Responds fast!
avg. 1 hour 35 minutes

from $250 / night

(2) Excellent 

19

Home rental in East Hampton

Hamptons / East Hampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Location, location, location! In its ideal location on a charming, quaint cul de sac in beautiful East Hampton Village, this brand new 4-5 bedroom, 4½ bath vacation home has it all. Luxury, luxury, luxury! Its amenities include a heated swimming pool, central air-condi …see more

from $1,100 / night

$5,650 - $14,950 / week

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from $1,100 / night

(3) Very Good 

9

Vacation apartment in Bellmore

Long Island / Bellmore

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children
Enjoy Long Island's pristine beaches, listen to an outdoor waterfront concert at Nikon theater venue,or relax in the back yard of this decorator furnished one bedroom/one full bath apartment situated on a canal. Spectacular sunsets. 45 min by train to NYC and 30 min fro …see more

from $150 / night

$875 / week

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Responds fast!
avg. 40 minutes

from $150 / night