Middle Island Vacation Rentals

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Browse Select Middle Island Vacation Homes

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

9.2 out of 10, Wonderful, (22)
"its small but very nice for a short stay would recommend."
The price is CA $136
CA $226 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Waterfront Westhampton Haven: Pool & Private Beach

10.0 out of 10, Exceptional, (1)
"The location was great, walking distance to the beach, beautiful sunrises/sunsets and not too much traffic on Dune road. The views were amazing and the second level was a perfect entertainment area. We loved how many bedrooms and bathrooms the house had - made it easy to get ready quickly! The property manager was so responsive and helpful to anything we needed! "
Waterfront Westhampton Haven: Pool & Private Beach

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (184)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

9.8 out of 10, Exceptional, (66)
"Great location right on the beach!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (65)
"Very nice place for a family to stay"
The price is CA $1,099
CA $1,916 total
includes taxes & fees
Sep 1 - Sep 2
Newly Renovated Luxury Beach House Ocean Bay Park

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is CA $105
CA $230 total
includes taxes & fees
Aug 17 - Aug 18
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

10.0 out of 10, Exceptional, (6)
"The is great!!! Very convenient location and plenty to do."
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Amazing Rocky Point Retreat Overlooking the Sound!

9.8 out of 10, Exceptional, (73)
"Love staying at this comfortable house each year for Thanksgiving and the location is perfect! "
Amazing Rocky Point Retreat Overlooking the Sound!

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (82)
"Great location. Very peaceful. Great house"
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

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

10.0 out of 10, Exceptional, (34)
"Great place. Total of 7 of us travelled. Will absolutely use this property again. Thank you for everything!"
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

9.8 out of 10, Exceptional, (11)
"Beautiful property! Well stocked with essentials and perfect for our group with and age range o16 - 83"
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

Tranquil & Pet-Friendly Estate on Long Island!

10.0 out of 10, Exceptional, (6)
"We had a very enjoyable stay. The house was stocked with everything you would need.It was clean and neat.This house has lot of character. Idefinitely stay here again "
Tranquil & Pet-Friendly Estate on Long Island!

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

9.4 out of 10, Exceptional, (53)
"Great house, great location, excellent host"
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

Pet-Friendly Home w/ Hot Tub Near the Hamptons!

2.0 star property
10.0 out of 10, Exceptional, (2)
"cute little comfortable abode. my cousins and i enjoyed our stay. Thank you for your hospitality "
Pet-Friendly Home w/ Hot Tub Near the Hamptons!

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.8 out of 10, Excellent, (3)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is CA $687
CA $1,256 total
includes taxes & fees
Aug 11 - Aug 12
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Summer getaway

9.4 out of 10, Exceptional, (11)
"Beautiful home with a beautiful pool"
Summer getaway

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

The price is CA $310
CA $450 total
includes taxes & fees
Sep 4 - Sep 5
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (55)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY
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