For the 50+ Traveler

When traveling locally or globally, staying in a rental instead of a hotel or resort is a wonderful option. You really get local and learn the area. Plus, it can be much healthier on the budget. They are wonderful when traveling with large groups, kids, or if you want/need more space, And no matter which rental company you book with such as Air BnB, VRBO, HomeAway, Vacatia, or Luxury Retreats, you will find they come in all shapes and sizes. And do not be surprised if you see the same rental on all of the sites.

We have booked them for one night and for a month. We have booked five star hotel type rentals to ones that had no electricity. They are especially wonderful when traveling to remote areas where there might not be other forms of lodging available, such as a stay we had on the Yakima River in Washington. We were in a tack room of a horse stable near nothing but the river. Guess what? It literally had all we fresh eggs to make for breakfast, homemade muffins, and a sheep named Mable who woke us up every morning at our front porch.

We have stayed in a fourth floor walk up in Old San Juan in Puerto Rico with an amazing modern kitchen, views of two sides of the islands to die for, and a comfy two person couch swing in the living room. In Bali, there was a home with two terraces each with a pool and fresh breakfast delivered each morning.

Old San Juan Puerto Rico penthouse vacation rental.

But one of our favorites was a home on Prince Edward Island which sat right on the tidal waters. The house had a fabulous kitchen, enough bedrooms for all of my sisters, the kids, and my parents! We literally only left to go to the market, because the house had a fire pit, a great yard for kite flying and all of the canoes, kayaks, and water activities we needed. My kids even stayed in their first Air BnB in Europe at the age of 18 and have stayed in rentals from Austin to Hong Kong ever since.

In all honesty, vacation rentals are not for everyone. If you really like to be waited on and pampered, surround yourself in totally luxury with spas and restaurants and beach cabanas, and don't want to clean up after yourself, they may not be for you. You need know how you like to vacation and keep your expectations in check when doing vacation rentals. Regardless of which brand you use, these tips work equally well. There will just be different ways to prepare based on the type of property you opt for.

Prince Edward Island rental house!

Picking the Perfect Rental

Being sure you are actually getting what you see on-line and having all the parts fall into place is a scary prospect. But there are ways to help make sure you won't encounter any untoward surprises upon your arrival. And yes, we have heard the horror stories. Admittedly, we have had some not so wonderful experiences, but from those we have learned how to make sure you have the best experience possible.

Research the Owners. I tend to always start with seeing who the owners are and if they have a management company. Then I read their reviews and check all the different rental sites to see if the reviews are the same. Once I do that I dive in.

Ask Friends. I start by posting a question in my Facebook Groups and to friends to see if anyone has stayed in a rental in the area I am traveling to. And if so, do they have a rental they loved. These personal recommendations are the best in my book. They are based on friends I know and trust and that I appreciate the way they travel. I will often book right off of their suggestion.

Reviews. I dive into the reviews and make sure the people writing the reviews have the same expectations that I do of a rental, meaning are they the same sort of traveler. I do this by simply reading a few of the reviewers other reviews.

Management Company. If there is a management company, the rental ranks higher for me than an owner only, It gives me security to know there is a back-up company just in case the worse happens. You are not relying on one person.

Read the Fine Print. Be sure you read all the fine print. For example, the statement "some properties have" means that the person or company owns multiply properties and not all or them say come with kayaks. Another key word is "well-equipped kitchen". What are your exceptions of "well-equipped"? If in Belize or somewhere tropic, we expect a blender and grill, because you know...frozen cocktails and grilled fish you catch.

Verify the Location. Be sure to truly look at the exact location of the rental. Just because it says one neighborhood may not mean it is right there in the neighborhood. If you're renting a condo, be cautious of laundry if you are expecting it. Often, laundry actually means it is in the complex or nearby.

Ask Questions. The biggest tip when picking the perfect rental is to ask questions...lots of questions. Do not be shy and if they are bothered by your questions or you are not getting timely answers, move on.

San Juan Islands.


Booking is very specific and often different sites and properties have their own rules and booking policies. Here are the top tips when booking...

  • Check to see if the property is on different booking sites and decide which site's policies you are most comfortable with. Sometimes we have also found specials or different prices on different sites.
  • Read both the site's polices and the properties policy for booking carefully. Know all the rules and deadlines.
  • NEVER - I repeat NEVER book directly with the owner, even if after booking they offer a discount. Always use a third party.
  • Use a major credit card when booking. Do not set up automatic payment for your deposits and final payment. We did have one place ask for exact cash when we left for the full payment minus the deposit and that was fine with us.
  • Ask questions. Never be afraid to ask. Clarify everything.
  • If you have travel insurance or are looking to buy travel insurance for the trip, be sure that the policy covers rental properties, especially rental properties using third parties.

Before You Leave

There are a few things to do before you walk out that door...

  • Be sure you have all your information including a local phone number of the contact that is letting you in, an emergency contact, and an exact address. You will especially need this information for your Custom's form if traveling internationally.
  • Double check dates, payments, and the address.
  • Be sure to book any services you would like to have while vacationing, such as housekeeping, butler service, kitchen stocking, or others ahead of time.

What to Pack

What to pack is very dependent on the property type, amenities, location, how long you will be gone, and your style of traveling. Our long packing list has been edited based on these variables. You can also often supplement your needs with a concierge service, if you so choose. In Hawaii, we have our concierge arrange to fill the refrigerator from a local organic farm, so that we have fresh food when we arrive.

Based on where we are going to be, the remoteness, domestic or international, we also may pack a suitcase with snacks, oatmeal, and other must haves. We try to source our food locally, but often when we travel on holidays, stores or markets may be closed on the day we arrive, so we are sure to bring what we need to get by.


  • Tea
  • Tea Ball
  • Coffee (prefer to buy local, but bring some just in case)
  • Good general knife
  • Wine opener
  • Wine stopper
  • Champagne stopper
  • Salt and Pepper
  • Other must have seasonings

Also, based on where we are, like Belize, we travel with an empty hard shell carry-on bag. We stop off at the Duty Free shop on our way out and buy tequila, vodka, wine, and bubbly. We find it to be less expensive. The rum we buy locally.


  • Shampoo
  • Conditioner
  • Toothpaste
  • Aloe
  • Emergency Med Bag
  • Sunscreen


This list changes with location and you need to think about what you would want/need. Never assume that what they say will be there will be or the number of the item you would like.

  • Beach towels
  • Beach blanket
  • Laundry detergent
  • Dryer sheets
  • Dishwasher Soap
  • Dish Soap
  • Dish rag
  • Dish towel
  • Plastic bags of different sized
Prince Edward Islands mussels dinner.

During your Stay

Upon arrival, review the rental and take pictures of any damage or things you feel the owner or management company should know about. This can include damage, missing items, and/or anything that makes you nervous. Also, review what they said would be in the rental like beach towels. If not there, let them know right away so you are not charged. If there is someone on site when you check-in, make these things known and decide how to best handle it. They may deliver the items or you may ask for a discount based on them not being there.

Be sure to review the rental list of do's and don'ts, emergency info, and anything else the owners/management left for you. Also, take a quick look at the departure info so you have everything in order. You don't want to do this the day you are departing.

If there is a concierge service, you can use them for booking restaurant reservations, excursions, transportation and much more. We highly suggest using these services as these folks are generally well-connected and can make your vacation so much easier.

Farmer's Market finds for a well-stocked vacation rental kitchen.


We like to always leave the rental in good shape. All the towels in one pile, kitchen wiped down, trash taken out (if not part of the services), and any other little things you choose. If you have not arranged to meet someone at departure, take pictures before you leave. If you're in a full-service check-out, ask that your rental be checked prior to leaving.

After Your Stay

Leave a review. Let the owners, management company, and future renters know exactly how you felt about the rental. Depending on how you booked, it is beneficial to leave a review and request the owner or management to also leave a review about you. These are mutually beneficial for future rentals.