People often ask me why Chris and I stay in a rental villa/condo on some of our travels instead of a hotel, and if it’s much more expensive. We’ve done vacation rentals about a dozen times now in the last couple of years and the answer is that sometimes it makes more sense for us depending on the location and our plans, and no, it’s not necessarily more expensive! It probably just looks super fancypants when you see pictures of an amazing view or a pool with no one else in it, but I promise we’re not paying crazy prices or using any secret magic tricks. Well, I use some tricks to find good places, but I’ll share those with you.
For anyone who isn’t familiar with Chris and me, we are thirty-somethings who travel a handful of times throughout the year (about 5-6 times in addition to traveling to see family) and our travel budget is in the middle of the road when it comes to accommodations. The short answer is that we really enjoy staying in rental properties for beach and snow vacations, but in this post I’ll break down our process on the when, why and how.
When and Why Do We Rent?
For some trips, especially when the purpose is to unwind, we’ve found that we’re able to relax more when we have some space to ourselves instead of sharing common areas with strangers. I do love people-watching, but sometimes you want chill time by the pool, and other people want to yell and scream and “caaaaannonball” into the pool. At a rental villa, we’re able to control the vibe of our surroundings a little better – we can hang out poolside with our own tunes playing (I absolutely love the Jawbone Jambox for this), or have peace and quiet for reading and relaxing. I’m guessing the rental villa option might be nice for families, too, since you can let the kids be kids without worrying that they’re bothering anyone. Even Chris and I enjoy cannonballing guilt-free without disrupting anyone else. And speaking of disruptions, we’ve never encountered any construction noise while renting a private vacation home, but hotels seem to have renovations going on frequently and it’s harder to avoid the noise.
Staying in a rental home also immerses us a bit more into local culture since we come and go from a residence in a neighborhood, rather than from a cluster of hotels. I love the feeling of living somewhere new even if it’s only for a week, and it’s fun to pretend that the rental is your own home.
In addition to beach houses, Chris and I like renting condos for our ski trips since rentals usually get us closer to the lifts with great ski-in/ski-out access. Plus, we have so much stuff with us when we snowboard/ski that it’s nice to be able to spread out and have the extra storage space for coats, boots, and gear. No matter the location or rental type (ski condo, beach villa, etc.) you get a lot more space per dollar when you rent a vacation home instead of a hotel room.
On the other hand, if we only need a place to sleep (and not really to hang out), or if we’re going somewhere for a week or more but staying in multiple cities, we stay in hotels. And most vacation rentals have a minimum number of nights per stay, so sometimes a hotel is necessary for a shorter getaway. Hotels definitely have their place in our travels. For us it really just depends on the trip, and I do enjoy certain aspects of hotel stays. It’s so wonderful to have someone make the bed and replace the towels, and who doesn’t love a chocolate on their pillow at night? I also love finding boutique hotels and inns with interesting details. I stayed at a hotel once that included a yellow rubber ducky in each of the bathrooms (21C Hotel pictured below on the left). How fun is that? On our trip to Iceland this summer we’re staying in five different towns and I’m excited about some of the cute little Icelandic hotels where we’ll be staying.
How Much Does Renting Cost?
Here’s the big secret that isn’t a secret: staying in a vacation rental isn’t more expensive than staying at a hotel and sometimes it’s even more cost effective. Just to clarify though, I’m not comparing the costs of our rentals to a hostel or a budget motel. I’m comparing our costs to a nice hotel in the three- or maybe four-star range, but there is a huge selection in rental properties to accommodate almost all budgets. It’s going to be more expensive than a hostel or budget hotel stay though, and some amenities like a pool do increase the cost per night.
When you first look at the weekly cost of a rental, it might appear more expensive than a hotel room in some cases. However, you have to factor in a few things first to compare apples to apples. The final cost of a hotel room per night always incurs taxes and fees, and then you also have to figure in the cost of parking, internet access, eating most meals out/ordering room service, and amenities like laundry service if needed. The rental doesn’t usually have any hidden fees, but you’ll most likely need to pay sales tax, and a security deposit or cleaning fee (usually refundable if you don’t trash the place).
We get a lot more bang for our buck in a rental, especially when it comes to things like view, amenities, and square footage. Chris and I always go grocery shopping when we stay in a rental so that we can eat breakfasts and lunches “at home,” which saves a considerable amount of money. We’re able to do our own laundry as well. Plus, I usually look for a rental that is just slightly outside of peak season/in-season, in what is sometimes called the shoulder season, low season or off-season. The rates are often dramatically lower, and as a bonus, it’s usually the perfect combination of fewer crowds and good weather. (Note: I’ve also tried renting well into low season, but there are sometimes drawbacks to looking too far into the off-season. It’s “off” for a reason! The weather could be less than ideal or even problematic, like hurricane season in the Caribbean which we definitely have encountered.)
Also, if you are able to share a rental with another family, couple or group, obviously the price per square foot is even better assuming you rent an appropriate sized property. It’s usually easy to find rentals that accommodate anywhere from two to twenty people or more.
Full disclosure: a couple of times we have been lucky to score some great deals. One time we rented a villa in St. John two days in advance because our Outer Banks vacation had been thwarted by Hurricane Irene so I found a villa with a good last-minute deal. And on our most recent trip to Grand Cayman, we ended up in a bigger, nicer villa because the one I originally booked was sold before our trip and the new owners decided to live there year-round. That actually happened two times in the process! Apparently this was an extremely rare and crazy occurrence, so our awesome booking agent offered an upgrade at the same price we had already paid. It was just luck that I had been working through a rental company that time instead of directly with the owner like I usually do. So we did save some money on those two trips. We’ve also gotten in early on rentals that have recently come onto the market and aren’t yet charging their full potential. A couple of places have increased to a price range out of our budget after we’ve stayed there!
Now, when you factor in the cost of transportation we might be on different pages. I can’t stand the thought of going to a new place and not being able to go see the furthest corner of the country/island/state if I so desire. I will want a rental car no matter where I’m staying, so for us a car is always in our costs and is therefore a break-even in the hotel vs. rental equation. A hotel is more likely to be in a location that is walking distance or a short cab ride to restaurants and shops. They may even have a free shuttle. In a vacation rental, you most likely need to have your own car to get around.
How Do We Find Rentals?
I have several favorite sites to search for rentals including FlipKey, VRBO and HomeAway. I have also used Luxury Retreats (which sounds expensive and it can be, but they do have some smaller, less expensive rentals), and for our trip to Grand Cayman I used Grand Cayman Villas which I found during an online search for Cayman rentals. There are so many other sites, but these are the ones I’ve used.
I do a ton of research to find the perfect home. Often it gets to the point where I could probably get a job as a real estate agent for the area. Who has that kind of time though, right?! Well, I usually start early, as much as a year or so in advance and the research is fun for me so it’s practically a hobby. To narrow down the listings I just use the website’s filters (price, amenities, location, etc.) and I read the reviews for any red flags. I also search to see if anyone has blogged about their stay at a certain rental, or posted about it on any travel forums. Photos from regular travelers rather than professional photos are often a huge help to see what the place actually looks like without Photoshop. I also search to see if the rental has its own site – often times they do, and there may be more information and/or better photos.
Once I have a few places narrowed down, I put on my stalker detective hat and try to find each house on Google maps to see what the general location is like. Sometimes this takes some super-sleuthing since the exact address usually isn’t posted, but the general area is, and then I use some clues in the photos to figure out which house it is on the map – roof color, pool shape, and view. The map will tell me things like, how close are the neighbors? Are there restaurants/stores nearby? Is there anything potentially noisy in the area? What will the lighting be like throughout the day? (That last one might be a photographer thing, but seeing what direction the home faces might also tell you if the pool will be in the shade all day, or if you have a good chance of seeing some beautiful sunsets!)
Once we find a rental we like, it’s just a matter of booking which usually involves reviewing/signing a contract, paying a deposit (anywhere from 25-50% of the total fee), and sometimes paying a refundable damage deposit. Those three main search sites have an online payment feature that I prefer to use, but if the owner doesn’t offer booking through the site, I always try to pay with a credit card to have a little extra protection if something goes belly up. So far so good, but I’ll report back here if anything sour ever happens! We have two trips booked next year with rentals, and I’m always excited to see how it turns out (i.e., how good I did at finding the perfect place). I’ve also booked through full service villa rental companies, Luxury Retreats and Grand Cayman Villas, where the concierge/agent handles the payments and contracts for you. They can also help with the research if you need assistance finding the perfect rental for your needs.
So what do you think? Have you ever stayed in a vacation rental? What’s your preference? If you need any help getting started on your search, let me know and I’ll be happy to assist! (Disclaimer: Unless like, hundreds of people take me up on this offer.)
Update 11/9/2015: I’ve now added Airbnb to my travel tool belt! You can read about our Toronto and Edinburgh Airbnb experiences here.
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Out of concern for a lack of shade on the beach due to less foliage, we purchased a 
