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Compare 461 Vacation Homes in Middle Island with updated reviews, rates, and availability.

Beach Bungalow Ocean Beach

9.8 out of 10, Exceptional, (22)
"For several years our family-now numbering 13 people, from infants to 82, plus dogs-have taken long weekend vacations every October on Fire Island. We like the communities of Ocean Beach and Seaview because stores and restaurants are open, and there’s a terrific market in Seaview. Our search Focused on number of bedrooms and baths, with excellent reviews. Quite quickly we decided that Beach Bungalow in OB was perfect for us. We had some questions about bed setups and had easy and excellent...
Beach Bungalow Ocean Beach

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.8 out of 10, Excellent, (9)
"Clean, spacious home with an amazing pool in a quiet neighborhood. If you're looking for a quiet getaway a good choice!"
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool

A Quiet Place in the Hamptons

9.8 out of 10, Exceptional, (34)
"We had a very nice time. The house was exactly what we needed and was close to everything. "
A Quiet Place in the Hamptons

Beautiful Beach House with Large Swimming Pool in Ocean Beach

10.0 out of 10, Exceptional, (34)
"Wonderful vacation! House has everything you need and the location is perfect. Hosts are quick to respond to any questions. Would definitely stay here again!"
Beautiful Beach House with Large Swimming Pool in Ocean Beach

Exclusive location with spacious interior offering many amenities.

7.8 out of 10, Good, (7)
"Everything was exactly as advertised! We appreciated the space as it made our weekend extra special, location was especially convenient. Overall a great experience! Thank you."
Exclusive location with spacious interior offering many amenities.

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

10.0 out of 10, Exceptional, (74)
"What a great home base for my family during Thanksgiving week! This house is everything it says it is and more. I seriously felt like I was a guest visiting family for the week. Too many awesome accommodations to list. The view out of the back windows, the bright coastal vibe, the home/audio setup, the huge/clean hot tub, the insanely awesome master bathrom!! What a neat house! Thanks, Joe for making our trip to the area a memorable one!"
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (23)
"Overall, this was a great stay. The house was clean and as advertised. The location was perfect for us as we were visiting family in Lake Grove, Stonybrook, and Port Jeff. A few recommendations for minor improvements: more towel bars/hooks in the bathroom and an upgraded coffee maker. Regardless, we would happily stay here again when visiting Long Island. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (54)
"We got to the house and it was a lovely house, in a great location. The garbage outside had meat and other garbage not in bags. The storm door was broken which we fixed ourselves, the floor was full of sand, the air conditioner in the kitchen didnt blow cold air and the fan in the ktchen didnt work either, the remote was nowhere to be found. I think some of our money should be refunded."
Updated home in great location with spacious living & outdoor features

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

9.6 out of 10, Exceptional, (99)
"Perfect location for nearby wedding (Old Field Club in East Setauket) and for places to shop and explore. Beautiful view , comfortable for the 6 of us. Would stay there again."
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

The Lindsay Luxurious Estate: Heated Pool, Hot tub, Huge Yard

9.8 out of 10, Exceptional, (19)
"This beautiful home is set on a huge, quiet, private lot. Equipped with everything you need to enjoy a wonderful, relaxing vacation, you'll love it!"
The Lindsay Luxurious Estate: Heated Pool, Hot tub, Huge Yard

Spacious Home Located Close to Stony Brook!

7.4 out of 10, Good, (12)
"Great stay great people great costumer care definitely reccomend"
The price is SAR 1,499
SAR 2,697 total
includes taxes & fees
1 Jan - 2 January 2025
Spacious Home Located Close to Stony Brook!

Luxury oasis on a 1+ acre compound with private swimming pool and tennis court!

10.0 out of 10, Exceptional, (3)
"Enjoyed our stay look forward to renting again next year "
Luxury oasis on a 1+ acre compound with private swimming pool and tennis court!

Beach Bungalow: Nearby Beach, Yard w/ Firepit

9.8 out of 10, Exceptional, (13)
"Easly access to the beach"
Beach Bungalow: Nearby Beach, Yard w/ Firepit

🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

9.4 out of 10, Exceptional, (50)
"Great house great location"
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

Quaint Family-sized Home w/private beach — 5 minutes from wineries!

9.6 out of 10, Exceptional, (10)
"Excellent "
Quaint Family-sized Home w/private beach — 5 minutes from wineries!

Ocean Beach Getaway

10.0 out of 10, Exceptional, (8)
"We had a great time in Ocean Beach. House is clean and even nicer/larger than the pictures. It comfortably fit our group of 12 with the pull-out couch. Very close to downtown/ferry and short walk to the beach."
Ocean Beach Getaway
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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Other property types in Middle Island

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool
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.