Destinations Family Travelogue

7 Tips for Booking a Vacation Rental Instead of a Hotel

I first started exploring, and other vacation rental sites when we were plotting our trip to San Diego – it fell during ComicCon, and hotel pickings were slim and pricy, so I thought there might be a way to save money and land oceanfront. Alas, a last minute deal was impossible to come. But the idea of a rental instead of a hotel stuck with me, and for Hawaii, that’s exactly what we ended up doing, island hopping with a cushy, spacious residence to come home to every night — and given the large party (eight people, including Kavi), it worked out perfectly. We got a taste of what real life in Hawaii looks like, staying in a residential area, had access to a kitchen, backyard, hammock or hot tub, and got to stay in the heart of each locale, all while saving cash.

Plus, I have admit, house hunting on the web for home in other places really satisfies the real estate junkie in me – all without the big bucks or commitment!

When we started plotting our winter trip, our initial discussions included talk of all-inclusives (fun, but a bit flavorless), cities (New Orleans revisited? Soon, I hope!), and even Hawaii again (cost-prohibitive). But the bottom line was: warm, close, tropical, and preferably with a Spanish bent, since we were hoping for an immersive experience. Puerto Rico was perfect. And given that it would be us and Navdeep’s parents, we knew that the usual hotel set-up wouldn’t work. So I started checking those vacation rental sites again, and struck gold. You can too!

But there are some things to keep in mind your first (or tenth) time out.

  1. Know What You Want: Two bedrooms? Is one bath doable? Parking? Walkability? Beachfront? Smack in the center of the city? Kitchenette cool, or do you want granite and the works? These are all things to think about before you start perusing, so you don’t get swayed by the pretty.
  1. Be Flexible. I know, it sounds contradictory. But each space is unique, and you never know when you might stumble upon a gem. Maybe one bath for four adults will be fun! It might be a compromise worth making for a particular view or location. (Like smack dab in the middle of Old San Juan, for example.) Many rentals are flexible on sleep situations – a two bedroom may accommodate six, for example, if there are bunks or a sleeper sofa. But you have decide if you can live with the situation for however long you stay. Know what you and your party needs, and where you can compromise.
  2. Start Early! It may be possible to score a last minute deal – but it’s unlikely, especially around the holidays or in peak seasons. So as soon as you’ve got your destination and dates sorted out, start stalking the sites to see what’s available. Do a cursory search by destination without dates to see what the market looks like in that area, and then do a search for what’s available within your specific dates. Check out the major sites, like and, but also google the words vacation rentals and your locations because there may be other options (this worked for us for Hawaii). Email early – and if there’s a place that you’re into that may not have availability, check in anyway. You never know.
  1. Know the Rules. Read the fine print for each listing – because it may rule the place out for you ahead of time. Some places are totally not kid friendly. Others have a minimum seven-night stay. Or no parking. You get the point: check out the details to ensure that the particular rental will work for you. Make sure you look into neighborhoods too – even if you have to email in advance to know exactly where a rental sits. It’s smart to suss out safety and conveniences (like parking, grocery stores and restaurants) before you commit.
  1. Bend the Rules: If you’re really smitten with a place. Ask! You never know. If it’s a seven day minimum, but the space is available, it could work out to your advantage to just reach out. Ask about extra bedding or kid-friendly options if things aren’t clearly spelled out. For example, our rental owners offered up a portable crib when they found out we were traveling with baby.
  1. Checks And Balances. Create a personable profile so you get good responses to your requests — and expect the same from the rental owners. Read reviews to see if a place really lives up to its hype – and it may be smart to see if you can find the same place listed on multiple sites, to see if the reviews achieve consensus. If there are flaws (noise? Draftiness?), think about whether you can deal. And also observe how the owner treats you in early communications – after all, they’re courting your business. If they can’t be quick and courteous now, what will you expect from them later. Don’t forget, too, to read the fine print for each site – the rules and guarantees vary, as do built-in fees. Know what you’re getting into – and cancelation penalties (which may vary by property!) before you book.
  2. Leave a Review. Be kind, but honest — it helps you build you and the rental owner build up credibility on these sites, and also helps other travelers. Remember, travel is about community, and it counts here especially!

Have you booked a vacation rental before? What are your best tips and tricks?

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