Vacation Home Rentals 101
The vacation Rental
If you’re organizing a vacation with extended family, have children, or plan to travel somewhere for a significant period of time, chances are high you’re looking into a rental property. And for good reason: vacation home rentals offer a fundamentally different experience from traditional hotels—especially when you’re traveling with a group or hoping to stay put and be together.
Unlike hotel rooms that can feel disjointed and impersonal, a vacation rental gives your family the space to spread out, share meals around a dining table, relax in the living room after a long day, or gather for board games, movies, and late-night chats. It’s less about squeezing in sightseeing from morning to night, and more about creating a rhythm—cooking breakfast in your pajamas, letting the kids run in the yard, unwinding by the fire pit after sunset. It’s not just about where you go, but how you experience the time together.
We’ve enjoyed our fair share of vacation home rentals in the U.S. and abroad, and know that they come with a ton of advantages over hotels under the right circumstances. The benefits? More indoor and outdoor space, staying in a prime neighborhood for less money, enjoying a full kitchen, regular access to laundry, complimentary parking, and amenities such as a pool, hot tub, fire pit and more. Plus, you have the ability to fully settle in, which is a luxury when you’re staying put for a couple of weeks or more.
Starting the Search
So you’ve decided you’re at least curious about a home rental. Where to begin your search? That depends. Consider your desired type of vacation and/or location, number of adults and children, how many bedrooms and bathrooms, whether you are bringing a pet, “must have” and “would be nice to have” amenities, and your budget.
For a bird’s eye view of availability, there are two major home rental sites to suit nearly every budget: Airbnb and Vrbo. When utilizing the filters to narrow down your search, select “Entire place” under “Type of Place” to avoid shared homes. We recommend that you only click on your “must have” (not your “would be nice to have”) amenities to ensure that you keep your options as broad as possible to begin.
We also recommend that you google the location(s) you’re considering to assess whether there are real estate agencies and/or property management companies that offer vacation rentals. This is commonplace in summer vacation hotspots along the East Coast such as Nantucket, Martha’s Vineyard, and the Hamptons.
If you’re going the luxury route, reach out to reputable real estate agencies that operate internationally like Sotheby’s and browse bespoke rental sites that offer luxury amenities and concierge services such as Cuvée, Four Seasons Private Retreats, One Fine Stay, Time & Place, and Villas of Distinction.
Looking for homes specifically suited to your brood? Kid & Coe offers an expertly curated selection of kid-friendly homes around the world. We love their detailed home descriptions and how you can search by type of vacation (i.e. “island getaways” or “country retreats”) rather than only by destination. Many of their properties come equipped with lifesavers like playrooms, bunk beds, travel cribs, and more.
Ask around! You never know whether your neighbor’s brother or colleague’s aunt has just the kind of property you would be keen to rent.
reading the fine print
You found your dream rental and it looks like it’s available for your dates! Should you book immediately? Not without reading the fine print. Read all available reviews (yes, really) and trust your gut as you read through others’ comments. We can’t underestimate the importance of this step.
Do not be swayed by gorgeous magazine-like photos alone. Google the address or nickname of the rental to see if you can find alternative property photos. Some properties, for example, may be advertised by more than one real estate agency, or they may be listed on multiple rental sites. Especially if you cannot find alternative property photos, be sure to read through the rental’s written description to gain a realistic understanding of the property’s location, layout and amenities. I can’t tell you how many times we’ve arrived somewhere without reviewing the floorplan only to learn that the room we had designated for the kids was two steep staircases away from our own.
Confirm the precise location of the rental. An exact address may not be provided until contract time to protect the owner’s privacy, but you can typically discern it from a map or by doing some investigating on Google. How far is the rental from the places you want to experience? Will you walk or bike or drive? Are there markets, restaurants, and shops nearby? Is the road paved or dirt? Will you have privacy from your neighbors?
Especially if you are planning to work remotely, confirm that the property has cell phone reception and/or reliable Wi-Fi. This is a non-negotiable out in the Hamptons as well as other island locales known for having spotty connectivity.
Want to review a floor plan to fully appreciate the layout or don’t see something that’s not a deal breaker, but would be nice to have, like bicycles or a beach pass? If time is on your side, ask the rental agency, property manager, or owner before committing. And if you are staying somewhere longer than a week, consider negotiating a long-term stay discount.
Once you receive the contract for signature or are ready to click on the “Book Now” button, read the fine print. Make sure you understand and are comfortable with the payment plan, which typically requires an upfront refundable deposit of 10-50%. Fully review house policies regarding utilities, pets, additional guests, events, cleaning obligations, communication during the stay, and cancellation by either guest or owner. Ask questions about anything you do not understand or want to negotiate.
ARRIVING + DEPARTING
Prior to arrival, ensure you have made your final payment and received confirmation accordingly.
If you plan to mail or ship any items to the home in advance (we always pre-order items via Amazon, for example), run it by your contact first Is the property able to receive mail and/or packages? Are there any specific delivery instructions you need to follow?
Consider making arrival day easy on yourself by ordering grocery delivery from Instacart or another local service. Select a time slot at least an hour after check-in time. The last thing you want is an annoyed owner or groceries gone bad if they arrive too early.
Make sure you know the details of your arrival, including check-in time. Will someone meet you in person or is it a contactless check-in? Do you have your contact’s name and phone number? Do you have the appropriate codes to gain entry to the property and garage?
Upon arrival, do a thorough walk through and document anything amiss. Confirm that there is no furniture damage or pet stains, that utilities such as Wi-Fi, the pool heater, etc. are working properly, and that you have received any agreed-upon amenities such as paper towels, toilet paper, etc. If you come across any issues upon arrival or during your stay, reach out immediately to the property manager, realtor or owner to see if they can ameliorate them for you. The last thing that anyone wants is for problems to fester or for either of you to leave each other a poor review.
The evening before departure day, review the booking contract to confirm departure time as well as your cleaning obligations. It is standard practice for renters to begin washing sheets and/or towels, to run and empty the dishwasher, to discard any opened food and refrigerated items, to empty the trash and to lower the thermostat, among other requirements. Be sure to follow the property’s instructions regarding locking the home and/or returning keys.
Enjoyed your stay and/or have some critical feedback? It helps to leave an honest review and pay it forward.
