The Hamptons without the 4 hour drive. Architecturally significant Cedar Shake beach oasis on a private court with breathtaking views of the Great South Bay.
Relaxed beach vibes by design. The wide open floor plan with retractable floor to ceiling windows bring the outdoors in for costal living at its finest (and coolest!).
Enjoy the water views while floating in the freeform gunite pool with built in jetted Jacuzzi.
Poolside loungers
Welcome to your happy place. Outdoor covered porch with comfy couch, over-stuffed pillows and nothing to see for miles but, well, the sea.

Spectacular Montauk Beach House in Massapequa, LI

3 bedrooms·3 baths
Massapequa • New York
4.94(17 reviews)

$5,325.00 USD total for 5 nights

Oct 19 – 24, 2026

The Bay House Bellmore NYC 40 Mints Beach 5 Mints
1st Bedroom Queen Bed with Smart tv
The Bay House Bellmore NYC 40 Mints Beach 5 Mints
The Bay House Bellmore NYC 40 Mints Beach 5 Mints
The Bay House Bellmore NYC 40 Mints Beach 5 Mints

The Bay House Bellmore NYC 40 Mints Beach 5 Mints

3 bedrooms·1 bath
Bellmore • New York

$1,795.64 USD total for 3 nights

Oct 19 – 22, 2026

Waterfront Beach House 37 Min from New York City
1st Bedroom Queen Bed with Smart tv
1st Bedroom Queen Bed with Smart tv
1st Bedroom Queen Bed with Smart tv
2nd Bedroom Queen bed with Smart TV

Waterfront Beach House 37 Min from New York City

3 bedrooms·1 bath
Bellmore • New York
Cheerful 4 Bedrooms House in Nassau county
Cheerful 4 Bedrooms House in Nassau county
Cheerful 4 Bedrooms House in Nassau county
Cheerful 4 Bedrooms House in Nassau county
Cheerful 4 Bedrooms House in Nassau county

Cheerful 4 Bedrooms House in Nassau county

4 bedrooms·2 baths
Hempstead • New York

$1,215.00 USD total for 3 nights

Oct 19 – 22, 2026

Large Family Home in Dix Hills
Arrive to a lit house and porch lights with combo lock
20x40 inground pool with slide and gazebo
Pool diving board, ladder and slide in 9 ft deep end
20x40 bi-level deck with barbecue and generous seating

Large Family Home in Dix Hills

4 bedrooms·2 baths
Dix Hills • New York
4.95(61 reviews)

$2,882.00 USD total for 3 nights

Nov 7 – 10, 2026

Gray Queen Bedroom
Gray Queen Bedroom
Gray Queen Bedroom
Full bathroom
Gray Queen Bedroom

Gray Queen Bedroom

1 bedroom·1 bath
Dix Hills • New York

$1,052.00 USD total for 7 nights

Oct 19 – 26, 2026

Tiny Home Private, Students, Nurses, Tech
Tiny Home Private, Students, Nurses, Tech
Tiny Home Private, Students, Nurses, Tech
Tiny Home Private, Students, Nurses, Tech
Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech

1 bedroom·1 bath
Bay Shore • New York

$388.70 USD $308.59 USD total for 3 nights

Jan 2 – 5, 2027

Cozy 2br Private Apt, Pet Pal, Events, LTR-STR
Cozy 2br Private Apt, Pet Pal, Events, LTR-STR
Cozy 2br Private Apt, Pet Pal, Events, LTR-STR
Cozy 2br Private Apt, Pet Pal, Events, LTR-STR
Cozy 2br Private Apt, Pet Pal, Events, LTR-STR

Cozy 2br Private Apt, Pet Pal, Events, LTR-STR

2 bedrooms·1 bath
Bay Shore • New York
$130 – $185/ night(excl. fees & taxes)
Queen Bed: PetPally, Events & Long/Short Stay
Queen Bed: PetPally, Events & Long/Short Stay
Queen Bed: PetPally, Events & Long/Short Stay
Queen Bed: PetPally, Events & Long/Short Stay
Queen Bed: PetPally, Events & Long/Short Stay

Queen Bed: PetPally, Events & Long/Short Stay

1 bedroom·1 bath
Bay Shore • New York

$351.40 USD $342.12 USD total for 3 nights

Nov 8 – 11, 2026

Bay Shore: Queen Bed Pet & Work Friendly
Bay Shore: Queen Bed Pet & Work Friendly
Bay Shore: Queen Bed Pet & Work Friendly
Bay Shore: Queen Bed Pet & Work Friendly
Bay Shore: Queen Bed Pet & Work Friendly

Bay Shore: Queen Bed Pet & Work Friendly

1 bedroom·1 bath
Bay Shore • New York

$323.78 USD $315.32 USD total for 3 nights

Oct 19 – 22, 2026

Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Private 3Br Apt: King-2Queen -PetPally -LTR-STR

Private 3Br Apt: King-2Queen -PetPally -LTR-STR

3 bedrooms·1 bath
Bay Shore • New York

$718.28 USD $699.88 USD total for 3 nights

Nov 8 – 11, 2026

King Bed Retreat: Pet-Pally | STR • MTR • LTR
King Bed Retreat: Pet-Pally | STR • MTR • LTR
King Bed Retreat: Pet-Pally | STR • MTR • LTR
King Bed Retreat: Pet-Pally | STR • MTR • LTR
King Bed Retreat: Pet-Pally | STR • MTR • LTR

King Bed Retreat: Pet-Pally | STR • MTR • LTR

1 bedroom·1 bath
Bay Shore • New York

$439.80 USD $427.87 USD total for 3 nights

Nov 6 – 9, 2026

UBSARENAAPT
UBSARENAAPT
UBSARENAAPT
UBSARENAAPT
UBSARENAAPT

UBSARENAAPT

2 bedrooms·1 bath
Bellerose • New York

$5,030.00 USD $3,772.50 USD total for 30 nights

Oct 19 – Nov 18, 2026

Spacious 2-Bedroom Apartment Minutes from UBS
Spacious 2-Bedroom Apartment Minutes from UBS
Spacious 2-Bedroom Apartment Minutes from UBS
Spacious 2-Bedroom Apartment Minutes from UBS
Spacious 2-Bedroom Apartment Minutes from UBS

Spacious 2-Bedroom Apartment Minutes from UBS

2 bedrooms·1 bath
Queens County • New York

$5,100.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Kingdom Cove
Kingdom Cove
Kingdom Cove
Kingdom Cove
Kingdom Cove

Kingdom Cove

1 bedroom·1 bath
Queens County • New York

$5,100.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

View from entryway
Cozy Chic 2BR private guest suite (up to 4 guests) image 1
Cozy Chic 2BR private guest suite (up to 4 guests) image 2
please read these house rules before booking
Cozy Chic 2BR private guest suite (up to 4 guests) image 4

Cozy Chic 2BR private guest suite

2 bedrooms·1 bath
Queens • New York
4.83(99 reviews)

$4,625.00 USD $3,950.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Kingdom Cottage
Kingdom Cottage
Kingdom Cottage
Kingdom Cottage
Kingdom Cottage

Kingdom Cottage

2 bedrooms·1 bath
Queens County • New York

$5,250.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Cozy Northport Cape for Extended Stay, 2 Bedrooms image 1
Cozy Northport Cape for Extended Stay, 2 Bedrooms image 2
Cozy Northport Cape for Extended Stay, 2 Bedrooms image 3
Cozy Northport Cape for Extended Stay, 2 Bedrooms image 4
Cozy Northport Cape for Extended Stay, 2 Bedrooms image 5

Cozy Northport Cape for Extended Stay, 2 Bedrooms

2 bedrooms·1 bath
Northport • New York

$983.00 USD total for 7 nights

Nov 2 – 9, 2026

Newly Renovated | Clean | 2 Bedrooms Private Suite
Newly Renovated | Clean | 2 Bedrooms Private Suite
Newly Renovated | Clean | 2 Bedrooms Private Suite
Newly Renovated | Clean | 2 Bedrooms Private Suite
Newly Renovated | Clean | 2 Bedrooms Private Suite

Newly Renovated | Clean | 2 Bedrooms Private Suite

2 bedrooms·1 bath
Central Islip • New York
4.95(20 reviews)

$546.00 USD total for 3 nights

Oct 19 – 22, 2026

Where your summer begins—this is Windows on the Sea, just steps from the ocean & designed for effortless days by the pool, sunset cocktails on the deck, and unforgettable memories with your favorite people.
A warm welcome, even furrier than expected—little touches of charm await from the moment you arrive.
Between refreshing dips in the ocean, return to your personal oasis where every comfort has been considered. Your private deck's spacious design accommodates both intimate morning coffees and fun evening gatherings as the sun sets.
Gather your crew in the sun-drenched Great Room—open-concept, beautifully designed, and perfect for reconnecting after a beach day.
A master bath made for pampering—soak with a view and let the outside world melt away.

Windows on the Sea

5 bedrooms·4½ baths
Ocean Beach • New York
5(70 reviews)

$6,424.58 USD total for 7 nights

Oct 19 – 26, 2026

View from Jamaica Bay
New York City Vacation Rental
living room
New York City Vacation Rental
New York City Vacation Rental

New York City Vacation Rental

3 bedrooms·2 baths
Queens County • New York
4.8(112 reviews)

$8,225.00 USD $6,625.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Waterfront Home sunsets over Manhattan
Waterfront Home sunsets over Manhattan
Waterfront Home sunsets over Manhattan
Waterfront Home sunsets over Manhattan
Waterfront Home sunsets over Manhattan

Waterfront Home sunsets over Manhattan

3 bedrooms·2½ baths
New York
$275 – $375/ night(excl. fees & taxes)
Living room / kitchen
Beach
Bathroom sink
Boardwalk
“Tilt A Whirl “ Beach House -Parking for 6 cars

“Tilt A Whirl “ Beach House -Parking for 6 cars

3 bedrooms·1 bath
Queens County • New York
4.93(124 reviews)

$11,125.00 USD $10,030.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Charming Coastal Retreat 1BR image 1
Charming Coastal Retreat 1BR image 2
Charming Coastal Retreat 1BR image 3
Charming Coastal Retreat 1BR image 4
Outdoor lounge space

Charming Coastal Retreat 1BR

1 bedroom·1 bath
Queens County • New York
4.88(17 reviews)

$5,913.25 USD total for 30 nights

Oct 19 – Nov 18, 2026