Middle Island Holiday Rentals

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Holiday Rentals in Middle Island

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$272
includes taxes & fees
10 Dec - 11 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is AU$916
includes taxes & fees
20 Dec - 21 Dec
Modern Vacation home. Close to The Hamptons

LUXURY BAY SHORE HOME

2.0 star property
Bay Shore
2.0 out of 10, (2)
"DO NOT book this house! I booked this house for Thanksgiving day visiting family. I received confirmation and everything. However till the day of arrival I never received any instruction on checking in. I called multiple times and only got voice mail in spanish. Finally I received a message saying this house was no longer available several hours before checking in! We had to scramble to find hotel rooms for 10 people. It was totally unacceptable!"
United States
Yan
LUXURY BAY SHORE HOME

Cozy 2 bedroom retreat in long island

2.0 star property
Central Islip
8.0 out of 10, Very good, (2)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is AU$386
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 bedroom retreat in long island

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

Westhampton Beach
10.0 out of 10, Exceptional, (195)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

Ocean Beach
9.0 out of 10, Wonderful, (53)
"The location is superb, can’t do much better! Towards the end of the main strip for privacy but still right near the action that you come to Ocean Beach for. The rental was clean and stocked with essentials upon our arrival (definitely a life-saver) with the onsite washer/dryer a bonus!As for the property owner, I’m happy to report that this one is a pleasure… congenial, accommodating and professional from the start of the reservation process and onward.We are looking forward to returning next...
United States
Amy B.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

Cozy Country Cottage #3

Miller Place
10.0 out of 10, Exceptional, (29)
"Fantastic stay! "
United States
Michael V.
The price is AU$496
includes taxes & fees
9 Dec - 10 Dec
Cozy Country Cottage #3

Walk to Beach 2BR Near Dining & Shopping

Rocky Point
6.8 out of 10, (26)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is AU$356
includes taxes & fees
8 Dec - 9 Dec
Walk to Beach 2BR Near Dining & Shopping

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Bayport
10.0 out of 10, Exceptional, (89)
"A special place and love staying here in this lovely home - looking forward to our next stay!"
United States
Roxanne M.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

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.
The price is AU$251
includes taxes & fees
7 Dec - 8 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Home Away from Home – 3BR Retreat with Amenities

Hauppauge
10.0 out of 10, Exceptional, (8)
Home Away from Home – 3BR Retreat with Amenities

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Center Moriches
10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is AU$1,143
includes taxes & fees
29 Dec - 30 Dec
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Coram
9.4 out of 10, Exceptional, (6)
"Great first time doing Vrbo great experience would do again "
United States
Rodrigo M.
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Ocean Bay Park
9.0 out of 10, Wonderful, (32)
"This unit was great. It's clean, quiet, and centrally located. It comes with 2 bikes which is a huge bonus (the rentals down the street are 40/day). It also has beach chairs and towels which is nice. We would definitely stay here again. "
United States
Kevin E.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

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.
The price is AU$1,012
includes taxes & fees
7 Dec - 8 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

A Quiet Place in the Hamptons

East Quogue
9.6 out of 10, Exceptional, (39)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveller
A Quiet Place in the Hamptons

4-bedroom house in awesome Brookhaven with AC

Brookhaven
The price is AU$1,249
includes taxes & fees
1 Jan - 2 Jan 2026
4-bedroom house in awesome Brookhaven with AC

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.
The price is AU$5,424
includes taxes & fees
27 Dec - 28 Dec
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Bay Shore Vacation Rental ~ 7 Mi to the Beach

3.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1)
Bay Shore Vacation Rental ~ 7 Mi to the Beach
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

Everything you need to know about Middle Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middle Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middle Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middle Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middle Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middle Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middle Island holiday rentals we have selected for you start as low as AU$251 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middle Island rentals

At Expedia, we put the best Middle Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middle Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middle Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middle Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Modern Vacation home. Close to The Hamptons: This holiday home rental outside of Middle Island is located on the waterfront, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.