Search Vacation Homes in Middle Island

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Our top choices for Middle Island vacation homes

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
$546 nightly
The price is $624
Dec 30 - Dec 31
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
$144 nightly
The price is $165
Dec 27 - Dec 28
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
Calverton
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
$582 nightly
The price is $665
Dec 24 - Dec 25
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Peaceful private 2-bedroom house in Bayport.Amazing location!

Peaceful private 2-bedroom house in Bayport.Amazing location!
2.0 star property
Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
$195 nightly
The price is $223
Jan 4 - Jan 5, 2026
Total with taxes and fees
Peaceful private 2-bedroom house in Bayport.Amazing location!

Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball
Mastic
10.0 out of 10, Exceptional, (27)
"Excellent accommodations for a large family gathering.The home is inviting and comfortable. It offers many amenities and the host is very hospitable. "
United States
Maria C.
$1,611 nightly
The price is $1,841
Dec 30 - Dec 31
Total with taxes and fees
Hottub, ⛳️, htd pool, Sauna, Basketball

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
$463 nightly
The price is $529
Jan 1 - Jan 2, 2026
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
$520 nightly
The price is $594
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern Vacation home. Close to The Hamptons

4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons
2.0 star property
Calverton
$730 nightly
The price is $834
Jan 5 - Jan 6, 2026
Total with taxes and fees
4-bedroom beach house minutes from Hamptons

Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!
Lake Grove
7.4 out of 10, Good, (24)
"Had a nice 3 night stay. Very convenient to Stony Brook and plenty of retail/ restaurants within 1 mile. "
United States
Jacki C.
$707 nightly
The price is $808
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious Home Located Close to Stony Brook!

The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Bella Vista St James! Waterfront house with a beach dock and so much more!
Saint James
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
$1,801 nightly
The price is $2,057
Dec 24 - Dec 25
Total with taxes and fees
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 2BR House Near Stony Brook University and shopping, fully renovated
2.0 star property
Stony Brook
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
$594 nightly
The price is $679
Jan 19 - Jan 20, 2026
Total with taxes and fees
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 4BR house near Stony Brook University & Hospital

Stylish 4BR house near Stony Brook University & Hospital
2.0 star property
Stony Brook
$747 nightly
The price is $854
Jan 12 - Jan 13, 2026
Total with taxes and fees
Stylish 4BR house near Stony Brook University & Hospital

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9)
"Wonderful stay"
United States
Kenneth B.
$802 nightly
The price is $917
Jan 4 - Jan 5, 2026
Total with taxes and fees
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (2)
"awesome house and awesome host"
United States
Matthew M.
$1,920 nightly
The price is $2,193
Dec 26 - Dec 27
Total with taxes and fees
5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Nature Meets Village - Walkable Northport

Nature Meets Village - Walkable Northport
Northport
$639 nightly
The price is $730
Dec 29 - Dec 30
Total with taxes and fees
Nature Meets Village - Walkable Northport
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.
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Top Middle Island Hotel Reviews

Find out more about Middle Island

Middle Island Vacation Homes information

Number of reviews
143
Accommodation
550 Vacation Homes
Lowest Price
$165
Highest Price
$2,193

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