Updated: December 2017

Vacation Rentals:

We all like to take vacations but not all of us own a second home or vacation home. Most of us end up booking a hotel room at a resort and pay extravagent fees just to take our family somewhere decent. In recent years I have been moving away from hotels and resorts and going with vacation rentals by owners or property managers. With a family of 4, we have found that renting a 2 bedroom condo or similar is a better deal financially than staying in a hotel where the accommodations are crowded and the rooms are small. We also get access to kitchens, often 2 bathrooms, and a family room to settle down in at night. My kids do like hotels, don't get me wrong, but the added space and freedom of renting a condo or house while on vacation has given me the peace of mind I need after a busy day. Now, instead of sharing a 2 queen hotel room, I can have the kids go off to bed in their room and I can enjoy the rest of the evening relaxing with my wife.

The Internet has done wonders for vacation rentals offered by owners. There are now dozens of websites that cater to travelers looking for this type of accommodation and with increased competition, the booking rates at many of these rentals has actually come down in price. The few exceptions are places like Hawaii and major ski resorts where demand outpaces supply and the owners don't need to lower their rates to get customers. Perhaps the most extensive site is VRBO.com (Vacation Rentals by Owner) which we feel is the original and largest vacation rental site on the web. There are something like 95,000+ rentals in every state and almost every country around the world. Homeaway.com and Vacationrentals.com are two other sites that I like to view periodically to see what is being offered. The good news is that there are literally dozens of rentals in almost all locations so you can choose from a variety of layouts and sizes - 1 bedroom condos, 2 bedroom townhouses, 5 bedroom luxury homes, etc. Most sites give you a brief description of the vacation rental with pictures and most importantly an online availability calendar so you can quickly check for vacancy on the dates you want. Just call or email the owners for any other information and to book your vacation. Often they request 1/2 the payment up front and then the other portion 30 days before your rental starts. I have personally rented about 10 properties over the last 5 years by using these online websites and finding the perfect situation and rental for my family.

Top Destinations:

People like to travel all over the world, but inevitably there are particular places to draw the majority of visitors. Hawaii is one of the top destinations for many in the United States as it offers up warm weather, sunshine, and a beautiful landscape of beaches, oceans, and lush interiors with incredible mountains and waterfalls. Maui, Kauai, and Oahu are perhaps the most popular and many families seek out Maui and the Kaanapali and Kapalua regions. Mexico is another favorite spot to visit with Cancun, Puerta Vallarta, and Cabo San Lucas waiting for vacation goers. Lastly, Florida has always been a top rated vacationing spot for families with their hundreds of miles of coastlines and the draw of amusement parks like Disneyworld. Vacation rental sites are loaded with affordable rentals that are within a few miles of all the popular things. VRBO has an extensive list of rentals in faraway places like Italy (Tuscany Villas), Paris (city lofts and apartments), and the Caribbean. You will find more availability for beach locations in the off-season when not as many people are traveling to the warmer weather. Prices will vary by almost 50% if you choose an off-peak month, so you can save money if you travel wisely.

Owner vs Property Management:

The vast majority of rentals we found on vacation sites are run by the owner and essentially save you the booking fees that property management companies charge when they handle the renting of someones place. I have found that renting through an owner is the best way to go, but there are issues sometimes at the rental property when you are actually on vacation, and you'll need to talk with someone local. It's always good to find out if the owner has a local contact for you to reach in case something goes wrong. It's hard to get things done renting a condo in Waikiki if the owner lives in South Carolina. Therefore, some locations are better served by property management firms that can service your needs in a timely manner. Overall, I think you will pay less by renting with the owner direct.

Best Rental Sites:

Which vacation rentals sites are the best? Do they offer the same services and choices? We scoured the Internet to find out these answers and more. Below we have listed the top destinations online for finding the ideal vacation rental through the owner. They are not necessarily in order of popularity, but each one offers something a little different than the other so check them out.
  • VRBO.com. Our personal favorite, this site has been around since 1995 and offers close to 100,000 vacation rentals. They are perhaps the original rental by owner website and they have grown dramatically over the years to now cover virtually every country around the world. Choose from destinations like Costa Rica, Fiji, Italy, Kenya, Australia, Hawaii, and Canada. Each listing has a webpage with photos, rates, descriptions, contact information for the owner, and in some cases a website with more information offered by the owner. You can quickly compare rates and see availability calendars to find out what dates are still open.
  • Homeaway.com. Great site for renting cabins, villas, condos, and vacation homes throughout the United States and abroad. The variety of vacation rentals is huge - get oceanfront condos, luxury mountain retreats, and large apartments in foreign cities. It's FREE to use and search their directory of owner rentals. Just type in the city or destionation and get a complete list of rentals. Properties list bedrooms, bathrooms, square footage, nightly rates, location type, owner phone number, amenities, and availability.
  • Vacationrentals.com. They have the perfect domain name. Their listings weren't as large as the 2 sites listed above them here. Still, quality rentals offered by owners at reasonable rates. The more popular destination spots like Las Vegas, New York City, Cape Cod and Orlando had plenty of rentals to choose from. The site is growing and will hopefully become a good alternative source to the other major vacation rental sites.
  • Vamoose.com. They claim to have over 250,000 listings. Their site layout is a bit different than the other sites we reviewed, but overall not bad. You can search by bedroom #, bath #, rental type (home/condo/etc), # of people it can sleep, or price range. With Google Ads on the site, we feel it's a touch more commercial in nature than we would prefer but I did like the way they wrote up on places like Mammoth Mountain in California with background information, weather details, and local events in the area.