Issue 4: A Guide to Finding Vacation Rentals
Tips on where to look and how to book, and links to recommended rentals
While I love a fancy hotel with my husband or friends, I usually hate a fancy hotel with my children. For families with kids, particularly younger kids, a vacation rental can be a much more comfortable option, and significantly less expensive than alternatives. Here are my top 10 tips for finding and booking great vacation rentals.
Treat VRBO and AirBnB Like Search Engines. I almost always start a search for vacation rentals by looking through properties listed on AirBnB and VRBO. These platforms generally offer a more comprehensive set of listings than other sites, and I love the option to save favorite listings on trip boards (on VRBO) and wish lists (on AirBnB). A key to using these sites though is to treat them as your first step in looking for a rental, rather than a one-stop shop.
Use the Filters and Sort Functions. AirBnB and VRBO each have their own strength, and it pays to look through both when searching for a rental. VRBO’s best function is the ability to sort listings by guest rating and number of reviews (unfortunately, you can’t do both at the same time). Filtering for price first before sorting further narrows results. The sort function can be a little tricky to find, but appears as a tab at the top right of listings as shown below:
AirBnB unfortunately does not have a similar function to sort by guest reviews. Two weaker alternatives are to search by the site’s credentialied “Superhosts” or to narrow your budget to a relatively small window to look at all listings.
Look for New Listings. One likely reason that AirBnB doesn’t allow users to sort guest listings by review is to avoid giving an outsize advantage to long-time hosts with more time to accumulate reviews. When I first started renting vacation properties, I only booked places with a high number of reviewers and exclusively 5 star reviews. While these places are generally great, there is (obviously) a lot of competition for them. I’m now better at figuring out what I am looking for in a property, and am willing to take a gamble on new listings, particularly if they have a great location, competitive price, or offer good space for my family or friends.
Find Local Rental Agencies. While AirBnB is the global giant for listings, local rental agencies can still have a larger number of listings for specific locations, particularly for popular beach areas in the U.S. It’s worth doing a quick search for local rental agencies or, even better, asking friends for recommendations. For example, we rented a great townhouse in Chincoteague, VA for a long weekend last spring through Seaside Vacations for significantly less than similar options on AirBnB.
Consider Timeshare Rentals. My husband’s parents are longtime timeshare owners, and we’ve had the privilege of staying in a couple of their timeshare units over the years. Timeshares are typically condos that offer a little more space than hotels (one and two bedroom units are common), kitchens, and laundry while still providing access to resort-type amenities like pools, on-site restaurants, and recreational activities. These features can make timeshares particularly attractive for families with young kids or tighter budgets. Though I have not yet used it myself, I have heard good things about Redweek, an online marketplace to rent unused timeshare weeks directly from owners.
Search for Alternative Booking Options. Flagging my most important tip. After searching for rentals on AirBnB, VRBO, and similar websites, take a minute to search the listing on the internet. Not infrequently, there are alternate or direct listing sites through rental agencies, management companies, or owners that can save you hundreds in fees.
Book (Far) in Advance. I book many vacation rentals 6 to 9 months in advance (which my spouse thinks is crazy). I’ve learned over the years though that affordable and unique properties go FAST. One trick is to read cancellation policies carefully, and consider negotiating the cancellation period. For popular rentals, owners are usually sympathetic to intervening life situations that can change vacation plans closer to the date since they can generally rebook without much trouble.
Let the Rental Dictate the Vacation (Sometimes). If you can be a little flexible about your destination, consider exploring rentals before picking a place. We have had a few off-the-beaten path vacations by going solely off the strengh of reviews for a rental. My favorite example is Smith Beach, a tiny private beach community about 15 minutes from Cape Charles on the southern tip of Virginia’s eastern shore. We spent a magical July 4 week here in 2017 in a small cottage on the water that we would have never found without a search for homes with unimpeacheable reviews.
Backyard of Smith Beach rental 2017, with beach just behind us.
Keep Rental Wishlists. When you find a great rental, keep track of it. I generally use AirBnB’s Wish List or VRBO’s Trip Boards features to do this, and keep a folder in my bookmarks for potential rentals outside of these two sources. Other strategies like a spreadsheet or an email folder to save links would work equally as well. Remember to ask friends and family for favorite places they have visited, and local rental companies they might recommend in areas they travel to regularly.
Look for Rentals When Searching for Resorts. Finally, even if you are more of a resort than a house rental person, it’s worth checking for rental properties near resort locations. These can be a bit tougher to find, so sometimes it’s worth working backwards and looking for a rental with resort privileges. Here is one example in Cashiers, NC that looks promising.
This issue comes with a gift: links to a few places I’ve rented or that are on my wishlist. Let me know if you have any favorites.
Rentals We’ve Booked
San Diego, July 2019, Solana Beach Rental. We stayed in this gorgeous, clean, and spacious three-bedroom condo right outside San Diego for a week. The location is excellent; we hit Legoland, the San Diego zoo, birch aquarium, and La Jolla and felt like we were never in the car for more than 20 minutes.
Chesapeake, VA, May 2021, Mathews Rental. We rented this house last Memorial Day Weekend, for our second time in Virginia’s sleepy but beautifical Middle Peninsula, on the Chesapeake Bay. House comes with a private pool and hot tub, kayaks, a fire pit, and private pier.
Lake Placid, NY, December 2020, Wilmington Rental. We keep coming back to Lake Placid, particularly for winter break vacations. Our last stay was at this unusual rental comprised of two suites in adjoining buildings with a private hot tub in between. Whiteface ski resort was a 5 minute drive while downtown Lake Placid was 15 minutes away.
Rentals on My Wishlist
Great house that can be shared with another family in Topsail Beach, NC.
Eyeing this spacious two bedroom in Capitol Hill walkable to the best parts of DC for friends and extended family visiting my beautififul city.
Gorgeous two-bedroom cabin in the Catskills with lake, waterfall, and forest reserve with hiking trails in walking distance.
A country beach cottage in South Kingstown, RI.
This tree house in Costa Rica looks awesome.