Middle Island Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Middle Island

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

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is AU$1,504
includes taxes & fees
31 Mar - 1 Apr
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (31)
"The mansion is beautiful, with large rooms in the upstairs bedrooms. The 2 bedrooms in the basement were a bit small and a bit Spartan. The fireplace room had 4 remotes, none of which worked the large screen tv, and half of the bedrooms had remotes that did not work the tv's. The kitchen silverware drawer was filthy, requiring my wife to clean the draw and was the silverware. The pocket door in the kitchen was off the track (not a big issue), however it requires repairing, The lower draw in the...
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

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

10.0 out of 10, Exceptional, (168)
"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."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (14)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is AU$2,467
includes taxes & fees
23 Mar - 24 Mar
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

10.0 out of 10, Exceptional, (11)
"The property was as advertised. It was clean and there was plenty of room for my family of 4. The place is updated and has large tvs in each room. We all agreed that beds were awesome and made for a great nights sleep. The location was close to major highways, making it easy to get anywhere we needed to go. I would definitely stay here again. Thank you for a great stay!."
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

10.0 out of 10, Exceptional, (21)
"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!"
Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

"Lots of space, great location, suited our extended family well."
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (14)
"Great stay great people great costumer care definitely reccomend"
The price is AU$1,163
includes taxes & fees
23 Mar - 24 Mar
Spacious Home Located Close to Stony Brook!

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

8.6 out of 10, Excellent, (10)
"The place was nice for our time with family for a holiday celebration. Our favorite space was the kitchen dining area which was large and well equipped. There was an issue with the heat upstairs; the hosts endeavored to respond to the problem in a timely manner. (Owners were on site for some of our stay, but it did not affect our activities.) Furniture comfortable....most rooms very lightly furnished. I would recommend bringing extra bedding as most beds only had a light quilt without sheets or...
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

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

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

Waterfront house next to Bellport golf course

10.0 out of 10, Exceptional, (11)
"From booking to departure it was perfect. Very lovely and comfortable home, we were very happy "
Waterfront house next to Bellport golf course

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

9.8 out of 10, Exceptional, (57)
"My friends, partner and I stayed over Columbus day weekend and were pleasantly surprised with the heated pool still being open, which was a huge highlight. The house was super clean and had everything you would need. We did have a minor issue with the hot water not working in the cottage, but other than that everything was great and we would defintely stay again!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

Stylish Sunset Retreat: Near Beach, Pool, Hot Tub

9.4 out of 10, Exceptional, (17)
"Overall 👍👍👍👍 Perfect area and vicinity to our wedding venue very nice neighborhood house was perfect unfortunately had to leave a day early due to New York City Marathon. ** Will definitely try to rent in the summer months"
Stylish Sunset Retreat: Near Beach, Pool, Hot Tub

Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

7.6 out of 10, Good, (9)
"It was as cute as it looked on-line and gave us a great space for hanging out and enjoying each other's company. That said, I would recommend that you rent this with loved ones as privacy is limited because of the indoor design. With no insulation or dry wall every noise is heard throughout the house! Other nice surprises: new AC units (very quiet), very comfortable beds, and an outdoor shower with good light. The street is very quiet. I was surprised that basic kitchen supplies weren't included...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

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

10.0 out of 10, Exceptional, (66)
"Great location. Great house. Close to ocean and bay. House was fully stocked with kitchen utensils so we could make large family meals. Two nice sized bedrooms. Third small bedroom had 4 bunk-style twin beds. Fourth bed was a loft accessible by ladder. "
Bungalow in Ocean Bay Park Fire Island- short walk to beach and restaurants!

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (14)
"Very clean and comfortable "
The price is AU$433
includes taxes & fees
26 Mar - 27 Mar
Cozy Country Cottage #3

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

10.0 out of 10, Exceptional, (84)
"Place was beautiful. It was very clean. Easy to get to. Would stay again"
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

House on the bay!

House on the bay!
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.
Don't see what you're looking for?
See all available properties in Middle Island
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middle Island you may be interested in

Radisson Hotel Hauppauge-Long Island

3.5 star property
6.2 out of 10, (1007)
"This hotel fit the needs for the days I was there. I have to say, it was extremely convenient; there’s a gas station and somewhere to eat directly across the street. "
The price is AU$209
includes taxes & fees
16 Mar - 17 Mar
Radisson Hotel Hauppauge-Long Island

Hyatt Regency Long Island

3.5 star property
8.2 out of 10, Very good, (1000)
"The view and the hospitality."
The price is AU$247
includes taxes & fees
11 Mar - 12 Mar
Hyatt Regency Long Island

Hampton Inn Long Island-Brookhaven

2.5 star property
8.6 out of 10, Excellent, (1004)
"It was a good stay in general, and easy to stay there while attending the nearby Doctor Who convention."
The price is AU$187
includes taxes & fees
3 Mar - 4 Mar
Hampton Inn Long Island-Brookhaven
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.

Frequently asked questions

Can I find holiday rentals in Middle Island?

Yes, there are holiday rentals close to the most popular sights in Middle Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middle Island has to offer?

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms: This holiday home rental outside of Middle Island is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals will I find in Middle Island?

Expedia has 3 holiday rentals for your stay in Middle Island.

What can I see and do in Middle Island?

While exploring the area, visit family-friendly sights like Long Island Game Farm, or get outside and enjoy nature at Carmans River. Brookhaven National Laboratory and Lasorda Legacy Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Middle Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middle Island. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.