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How to Find the Perfect Rental Home for a Luxury Summer Vacation

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha's Vineyard

We don’t know about you, but as soon as the first day of spring arrives, we start dreaming about summer. And sometimes that means we start daydreaming about renting a home for summer vacation. You know, a place with a pool, a great kitchen, an easy walk to the beach and a well-stocked library. If you’re similarly situated, and ready to find your summer home away from home, we’ve got some suggestions. Our ace correspondent Julie Chang Murphy is sharing her expert tips on how to find the perfect luxury rental home this summer 2022 in elite vacation destinations like the Hamptons, Nantucket and Martha’s Vineyard.

its that time of year again: the summer house search

Dreaming about summer sun and sandy beaches in the Hamptons, Martha’s Vineyard or Nantucket? Even though it may not feel like it at the moment, summer vacation season will be here in a matter of weeks.

Which means that if you’re planning to rent a glorious luxury house for the months of July or August, or for the entire summer, then it’s time to get moving. In our luxury summer home rental series, we’re sharing insider tips on how to find the right rental property, and also specific insights and information on rentals in each of the iconic East Coast summer vacation destinations.

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First up? The process for finding a dream luxury summer rental irrespective of destination.

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha's Vineyard

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha’s Vineyard.

how to find the perfect luxury rental home for summer vacation this year

Based on our own experiences, and conversations with experienced luxury property renters, if you’re looking to kick it like a boss this summer, here’s the inside scoop on the 9 step-process for finding the perfect luxury summer rental.

1. Narrow your search.

Before you start looking for actual properties, have a specific destination in mind. That seems like a no-brainer but what we mean by that is – narrow it down to the town, the neighborhood, and even the streets if possible. Just imagine searching for a spot in lower Manhattan…The Lower East Side is very different from Soho which is worlds apart from the FiDi.

As we’ll share in our posts about Martha’s Vineyard, Nantucket and the Hamptons, various towns and neighborhoods have vastly different types of housing stock and wildly differing vibes. Do your research up front so that you find your “tribe.” Then, if you can’t find a dream rental in your ideal sweet spot, move outward in concentric circles until you find one.

A scattershot approach won’t work in this pursuit – the more clarity you can bring to your search, the faster and more effective it will be. And if you’re renting to see if you want to purchase a summer place, all the more reason to micro-target your ideal house.

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha's Vineyard

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha’s Vineyard

2. Book early!

Many people begin planning their summer vacations and researching rentals in January. For the largest selection, start early. Unlike properties at lower price points, waiting is not likely to net you a significant price break on a luxury rental. If you hold off until May, you’ll be left with an array of underwhelming properties, not discounted gems.

3. Work with a broker.

Even in this modern era, special and highly expensive properties don’t always show up on generalized online listings. In the tony summer resort towns of East Hampton and Edgartown, for example, many choice properties are still rented via a local brokerage team, who knows the location cold because they’ve been brokering rentals and sales there for decades (and of course, they do have websites).

To find the right broker, ask trusted friends and look at listings. It will quickly become clear which 2-3 brokers are “the ones” for the kind of home that you have in mind. These brokers will all have websites – it’s just that when the time comes, you’ll have a real person to talk to, who can serve as an intermediary between you and the property owner.

4. Don’t dismiss online resources.

If you just can’t manage another relationship in your life and prefer to do it yourself, the online luxury rental market has evolved from all those Airbnb horror stories you might have in mind. In fact, Airbnb Plus offers a selection of only the highest quality homes that have been verified via a 100 point check system for upscale design and comfort.

Other sites like Onefinestay, Villas of DistinctionLuxury Retreats offer luxury homes with the added benefit of a 24/7 concierge service that can arrange bespoke local experiences and assist you in organizing airport transportation, private chefs, and grocery deliveries. The comforts of home with the service of a five-star hotel! We may never leave.

5. Be clear about your priorities.

Right on the beach? Or close to town? Pet friendly? What about smoking? Will you be doing a lot of entertaining? Does everyone have to have their own bedroom? What about a pool and tennis court? No property is likely to check every box, so be clear about what things are necessities for you and your housemates, and which ones are only nice-to-have.

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha’s Vineyard.

6. Visit the potential properties in person. 

Make a trip to your destination off-season to look at your options in person if at all possible. It’s a major investment of time and money, but it’s totally worth it. Surprises are great fun, but not on your precious summer vacation.

Finding the best rental is not so different from finding the right home to buy – you can narrow your list of options by viewing listings and photos. But the only way to be sure is to experience it in person. If you’re going to be spending $75,000+ a month for summer rental, you really don’t want to get it wrong.

One of our friends just returned from Martha’s Vineyard, where she viewed three properties and finalized an agreement for a summer rental. Sure, it was hassle to fly there in early March – but now she can sleep well at night. BTW, once you find a property you love, try to negotiate with the owners at the end of the summer for next year while you’re still there.

7. Make sure you have beach access rights.

In some elite communities, like East Hampton, you cannot park near the beach unless you have a beach access pass. You may be able to lay out on the beach, but there won’t be anywhere within walking distance to park your car. If you care about that, be sure you know which beaches you’ll have parking and personal access to before you finalize your rental decision.

8. Read the fine print.

Be sure that you know if there are activities that you aren’t allowed to conduct on the rental property, and also what the damage and liability insurance coverage entails.

Know from whom you’re renting – owners are likely to do background checks on you, and you should be sure that you get all of your questions about them answered, as well.

Cancellation policies, security deposits, and the like are all key contract terms. Have your attorney look the rental agreement over, especially if you’re doing this for the first time – once you sign, it’s a legally binding document, so take it seriously. Be sure you know the local handyman, plumber, pool service, tennis court maintenance and gardeners used by the owners, and be sure that you know which of those services are included in the rental fee. If you have small children, request a safety audit to ensure that smoke alarms are in working order and balcony heights adhere to regulations.

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha's Vineyard

How to find the perfect luxury rental home this summer 2022 in elite vacation spots like the Hamptons, Nantucket and Martha’s Vineyard.

9. Consider buying travel insurance.

Renting a summer villa is a substantial investment. Some insurances can cover you in case of bad weather delays, medical evacuation and even job loss. When it comes to peace of mind, it’s worth the extra money to not think about potential doom and gloom.

how to find the perfect rental home for summer vacation this year

There you have it: nine steps to summer vacation rental bliss. Good luck! You’re gonna nail it.

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This article contains affiliate links to products independently selected by our editors. As an Amazon Associate, Dandelion Chandelier receives a commission for qualifying purchases made through these links. 

Crediting her training as a cultural anthropologist at Wellesley College, Julie has immersed herself in various industries in the last 15 years including fashion design, event planning, and fitness. Julie lives in New York where she loves trying every ramen and dumpling restaurant with her husband and three children. She finds joy in bold prints, biographies of fierce women, kickboxing. And spending way too long finding the perfect polish color to express her mood.

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