Photo by Erisa Dilo
The Heights vacation rentals
We found 29 vacation rentals — enter your dates for availability
Discover a selection of 12 homes and other vacation rentals in The Heights that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, such as a fireplace and garden. At the end of the day, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
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Find the best place to stay - The Heights
Showing deals for: Oct 12 - Oct 15
Relax and Enjoy!
Sleeps 10 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is $1,371
$1,371
Fees included upfront
Chic Shelter Island Home, Pool and Gardens
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is $1,808
$1,808
Fees included upfront
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
The current price is $544
$544
Fees included upfront
Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is $1,478
$1,478
Fees included upfront
Kick back and unwind
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is $605
$605
Fees included upfront
Waterfront Greenport Condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.08.0 out of 10
Very Goodvery good
1 review(1 review)
The current price is $384
$384
Fees included upfront
Top rated rentals - The Heights
Family Reunion
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Amazing 🩹
Ellen S.
Stayed Jun 2025
Nice place to hang out
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Pool area with speakers is a great place to spend time. House is very comfortable place to spend time.
BOB T.
Stayed Sep 2024
Fantastic house
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
This is a fanstastic house, beautifully decorated, and fully outfitted with everything you need. The owner is great--he checked in on us several times to make sure we had everything we needed, which we did. I have rented many VRBO homes, and this one is the best.
Emily C.
Stayed Jul 2024
Great stay
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Sal was very communicative and hospitable. House was great and we had a great stay
Jodi J.
Stayed Jun 2024
Gingerbread Cottage
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
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Allison R.
Stayed Sep 2023
Calm, Peaceful, Wonderful
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The care and condition of this house makes it clear that it's well loved, and now we love it too! We spent four weeks in this cozy place, and the house was a peaceful oasis throughout. We're already missing the spacious screened porch / outdoor room at the back, and we hope to return again.
The house is meticulously clean and well stocked. The neighborhood is quiet and calm. The grounds are spacious and well landscaped. Judy was lovely as well—thoughtful, considerate, and just the right amount of communication.
We loved it and will certainly be back.
Josh C.
Stayed Aug 2023
Great house and nice location
1010 out of 10
Exceptionalexceptional
1 review(1 review)
This was such a great spot for our wedding party. We really enjoyed our stay and the house was even better than expected.
Elizabeth G.
Stayed Aug 2021
Family Getaway
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Virginia was a wonderful and incredibly accommodating host! Our family of 7 (plus one infant) fit comfortably in this clean and welcoming home. The pool was always at the perfect temp and everything one could possibly need for a family getaway was right within the home. Highly recommend!
Shanna Z.
Stayed Jul 2021
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Find out more about The Heights
Frequently asked questions
What is the most popular type of vacation rental accommodation in The Heights?
Condos are the most popular type of vacation rental in The Heights, according to our data. Even if you have a different idea about what you want, Vrbo has properties in loads of shapes and sizes. Look through our options to find your ideal match.
How much does it cost to rent a vacation rental in The Heights?
A number of things can influence the price of a vacation rental in The Heights, such as the time of year, length of stay and property type. However, all our vacation homes have one thing in common --- amazing value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in The Heights?
Prices for beach houses in The Heights will vary depending on the size and type of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to view your vacation rental options and prices. From there you can use the filters to narrow down your search by ratings, amenities and more.
Are there pet-friendly vacation rentals in The Heights?
There certainly are. You can choose from 11 stays that allow pets in The Heights on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to find a property where your puppy dog can lap up the fun.
Can I rent a house with a pool in The Heights?
Mark the "pool" box in our filter tool and pick from eight houses with private pools in The Heights on Vrbo. Lazy soak or ball games and races? Downtime is up to you when your Vrbo vacation home comes with its own swimming pool.
What are popular rental amenities in The Heights?
A barbecue grill, a swimming pool and a beach view top the list of most popular rental amenities in The Heights. Whether you're heading away on your own, with a partner or as a family, Vrbo will help you find a vacation home that suits your style with all the conveniences you're looking for.
Are there large group vacation rentals in The Heights?
You can choose from three vacation rentals in The Heights that can sleep 10 or more people. Whether you're planning a get-together with extended family or a celebration like an anniversary, there's plenty of room to get your loved ones together under the same roof.
Are there vacation rentals in The Heights that welcome kids?
With 11 family-friendly vacation homes to pick from in The Heights, there's never been a better time to introduce the little ones to the wonders of travel. Just check our "Properties good for families" filter to find stays that feature amenities ideal for traveling families, like living rooms, pools, hot tubs and entertainment areas.
What are the top attractions for families in The Heights?
Enjoy a day out with all the family at Shelter Island Country Club. This top attraction is close to the center of The Heights.
Are there vacation rentals with WiFi in The Heights?
Whether you want to stay in touch with world events, write a few emails or post a pic to social media, there are five vacation homes with WiFi in The Heights. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in The Heights?
You'll have your pick of 11 Vrbo vacation rentals with air conditioning in The Heights offering that cool, cool breeze and extra element of comfort. Simply enter your chosen travel dates and then use our filters to search for stays with air conditioning.
How old do you have to be to rent a vacation rental in The Heights?
Age restrictions can vary across properties on Vrbo, so check the rules of the vacation home in The Heights you want to book. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in The Heights for?
The amount of time you can stay in a The Heights vacation home for is up to each property. Simply put in your dates of travel to see options offering extended stays. They come with all you need to make your extended break more enjoyable and comfortable, like air conditioning and kitchens. Some Vrbo vacation homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in The Heights?
In The Heights, you'll find great deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a mini escape or a few weeks away, we have a host of options to suit your needs and budget.