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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 566 Vacation Homes in Middle Island with updated reviews, rates, and availability.

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Fridge, microwave, oven, stovetop

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very Good, (44)
"This house was in the perfect location as it was close to the ferry terminal and a short walk to ocean beach."
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (176)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
The price is AED 1,084
AED 2,266 total
includes taxes & fees
28 Apr - 29 Apr
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
🌞New Listing!! Ocean View Retreat!🌞
Terrace/patio

🌞New Listing!! Ocean View Retreat!🌞

9.4 out of 10, Exceptional, (21)
"Loved the bamboo flanked boardwalk getting to the cottage. Cute cottage with an amazing beach view"
🌞New Listing!! Ocean View Retreat!🌞
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
4 bedrooms, desk, iron/ironing board, free WiFi

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

9.8 out of 10, Exceptional, (57)
"Great location right on the beach!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Living area

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

10.0 out of 10, Exceptional, (26)
"Great place to stay. It was prefect for our family of six. We really enjoyed the stay and would stay there again. It was very clean and organized."
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
The Raabbit Hole
Fridge, microwave, oven, stovetop

The Raabbit Hole

9.2 out of 10, Wonderful, (22)
"Only recommendation would be to upgrade the beach chairs . The house was very Homie and comfortable and plenty big. Would definitely stay again. "
The Raabbit Hole
Hottub, ⛳️, htd pool,Basketball, volleyball . 10% book 2 nights
Outdoor spa tub

Hottub, ⛳️, htd pool,Basketball, volleyball . 10% book 2 nights

10.0 out of 10, Exceptional, (22)
"It was a very nice experience staying there. The owner replied to our questions pretty fast. I love the backyard, but unfortunately, it is too cold to stay outside during the winter. I would definitely recommend this house and we will try and go back in a warmer season!"
The price is AED 2,204
AED 4,792 total
includes taxes & fees
10 May - 11 May
Hottub, ⛳️, htd pool,Basketball, volleyball . 10% book 2 nights
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger
Outdoor pool, a heated pool

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

9.6 out of 10, Exceptional, (97)
"House was ideal for our extended family for thanksgiving weekend."
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger
Beach Bungalow Ocean Beach
4 bedrooms, iron/ironing board, free WiFi, wheelchair access

Beach Bungalow Ocean Beach

9.8 out of 10, Exceptional, (22)
"This was our second year with this house. Everything was great. We will be back next year for a third year. "
Beach Bungalow Ocean Beach
Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite
TV, fireplace

Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite

8.8 out of 10, Excellent, (20)
"The house was clean. Great communication with host. Would stay again!"
Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite
Fire Island Beach House - Atlantique
Property grounds

Fire Island Beach House - Atlantique

9.8 out of 10, Exceptional, (10)
"Location was perfect as a very short walk from Ferry port. Views over bay, was beautiful. Very well looked after by the owner. Had a wonderful time. 😊"
Fire Island Beach House - Atlantique
Mastic Beach Surf House
Property grounds

Mastic Beach Surf House

10.0 out of 10, Exceptional, (10)
"The house was relaxing and cozy. The perfect quiet get-away from the hustle and bustle of the city!!"
Mastic Beach Surf House
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"All went well, would stay again if in the area"
The price is AED 1,028
AED 2,048 total
includes taxes & fees
28 Apr - 29 Apr
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Spacious Gorgeous Getaway perfect for family reunion or business
Fridge, microwave, oven, stovetop

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business
2 Acres Gated Estate W/Pool,Hot Tub, Tennis, Basketball, Garden, Beach, Dog OK
Smart TV, fireplace, stereo, computer monitors

2 Acres Gated Estate W/Pool,Hot Tub, Tennis, Basketball, Garden, Beach, Dog OK

10.0 out of 10, Exceptional, (1)
"Perfect location, convenient to everything, house was clean and came fully equipped and the owner was easy to work with."
2 Acres Gated Estate W/Pool,Hot Tub, Tennis, Basketball, Garden, Beach, Dog OK
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
Smart TV, fireplace, smart speakers

Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!

9.6 out of 10, Exceptional, (12)
"Benny's house was a convenient and comfortable spot for our brief stay in the area, and the logistics couldn't have been easier."
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
Riverhead Farm House
Exterior

Riverhead Farm House

10.0 out of 10, Exceptional, (22)
"We had a wonderful time staying here. The house was great for our family. Loved the location. We would stay here again."
Riverhead Farm House
Bungalow in Ocean Bay Park Fire Island- short walk to beach and restaurants!
Terrace/patio

Bungalow in Ocean Bay Park Fire Island- short walk to beach and restaurants!

10.0 out of 10, Exceptional, (66)
"Very close to beach and close to market for any last minute items."
Bungalow in Ocean Bay Park Fire Island- short walk to beach and restaurants!
Amazing Rocky Point Retreat Overlooking the Sound!
TV

Amazing Rocky Point Retreat Overlooking the Sound!

9.8 out of 10, Exceptional, (69)
"Love staying at this comfortable house each year for Thanksgiving and the location is perfect! "
Amazing Rocky Point Retreat Overlooking the Sound!
Bellport/E. Patchogue, 4 Bed, 3 Bath, Waterfront.
Fridge, microwave, oven, stovetop

Bellport/E. Patchogue, 4 Bed, 3 Bath, Waterfront.

9.6 out of 10, Exceptional, (44)
"We stayed at Cabin 5 with a small group of family and teens who were in town for a sailing competition. The house was just what we needed and had more space than we expected or needed. The host was very helpful and communicative. A wonderful stay!"
Bellport/E. Patchogue, 4 Bed, 3 Bath, Waterfront.
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

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries
Smart TV, fireplace, video games, stereo

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10.0 out of 10, Exceptional, (86)
"Property was a great home base for a weekend getaway. Location and accommodations were great."
The price is AED 1,433
AED 2,711 total
includes taxes & fees
5 May - 6 May
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Outdoor spa tub

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (6)
"Robert was an amazing host..We had an incredible New Year’s Eve…We are already planning our next trip back… "
The price is AED 2,204
AED 4,314 total
includes taxes & fees
30 Apr - 1 May
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
Exterior

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

10.0 out of 10, Exceptional, (76)
"A gorgeous and peaceful setting for a wonderful week with family. Thank you so much for a fantastic stay - and looking forward to visiting again in the future."
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
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.