Family Vacation Planning and Renting a Vacation Home

Looking to rent a vacation home for your family trip?

Learn how to find a place your whole family can enjoy with amenities you’ll love, as well as how to spot red flags for where not to stay. Discover strategies for narrowing down potential stays with tips from frequent travelers to vacation homes.

Meet Your Guides

Danielle Riddle, travel expert and CEO of Inspired Travel Group, serves corporate travel clients with a luxury level of high-touch service. She believes that choosing a property takes research, research, and more research!

Danielle offers, “Knowing the area, activities, and how your family or group likes to spend their time on vacation is key to finding the best place to stay.”

Rick Newman, a serial entrepreneur and the CEO of UCON Exhibitions, runs one of Australia’s top exhibition stand design and build companies and spends most of his time managing logistics, construction, and tight deadlines.

“So when it comes to vacations, I take planning seriously. A bad rental can wreck a trip, and I am not one to leave things up to chance,” Rick says.

Tanya Turner, a full-time budget travel blogger at The T Word on Travel, has been an avid vacation rental user for over 15 years. She is a big planner and loves to budget when it comes to her family’s travels.

She conveys, “We are a family of 3; Mom, Dad, and young son. We work incredibly hard for our money, so it’s imperative that we book somewhere that we’ll be comfortable, happy, and safe.”

Alice Wu, PR Associate at Mind Meld Inc., loves to travel and enjoys planning vacations for her family of four, including two children aged 7 and 9.

Her top priority when traveling is finding activities of interest to her children that are affordable and easy to get to.

Planning Family Vacations

When it comes to creating an itinerary for her family, Danielle plans trips with specific destinations in mind, then narrows it down to an area based on a number of factors, including:

• activities (especially kid-friendly)
• restaurants
• proximity to tours or events for immersion in the local culture

Danielle adds, “Once I have an area outlined, I step into narrowing down specific properties available and which ones are best suited for my family of four, catering, of course, to our vacation non-negotiable factors.”

Tanya starts researching places about 12 months in advance. “I save listings and then check back regularly to see if hosts update availability on their calendars,” she quips.

For Rick, it’s more about time of year than anything.

He suggests, “Timing depends on the season. If it is a major holiday period, I will start looking six months in advance to get the best options. If it is a quieter time, I will book a month or two out. Anything last-minute is usually a gamble, and I would rather not roll the dice on whether the only available rental has decent Wi-Fi or a working air conditioner,”

“That being said, sometimes you get lucky—cancellations happen, and I have snagged some great places by checking at the right moment.” 

Not all vacations need months of planning to take flight, though.

Alice says, “Honestly, sometimes eight months in advance, and sometimes a week before. It all depends on how serious I am about going somewhere.”

Location, Location, Location

Rick confides, “If I am booking a vacation, I already know exactly where I want to be. I always do my research! Lake Jindabyne is a favorite when I want a mix of water sports and mountain views. It has the perfect balance—boating, fishing, and great hiking spots within a short drive.”

He takes his watersports seriously, noting, “I will not book something just ‘near’ the lake. If I am staying at Jindabyne, I want a place with direct lake access, not something where I have to haul gear five blocks every morning. Being right on the water makes all the difference.”

Tanya uses technology to determine if a neighborhood is where she wants to rent a vacation home, exploring the area virtually before committing to a choice.

She reveals, “I typically choose a general location (broad area) first and then narrow down the best areas based on safety and walkability. When I am in the research phase of looking at a location, I will often open up Google Earth to walk the streets, and I will even try to spot the rental based on photos (if I have no address).”

Alice falls into the “general” group when it comes to location, preferring to seek destination travel ideas from friends. She asked a travel-savvy friend, “Where in Europe should I go that’s not touristy and on the cheaper side?” He mentioned Bulgaria or Romania. From there, Alice relays, “I’ll get his input on where in Romania or Bulgaria, and whereabouts in those cities or towns, then I’ll start looking for family vacation rentals.”

Her ultimate destination depends on whether or not there are actual vacation homes for rent in the places her friends refer, not just hotels. If there aren’t any vacation rentals, she doesn’t book in that area and continues her search.

Alice offers, “I tend to plan for a city, then figure out what to do there. If the city doesn’t have much or the places are just way too expensive to book, I move on. I’m very flexible that way. I try to weigh affordability with activities that might interest my kids and how easy it is to get around.”

Prioritizing Amenities You Love

Going on vacation with children means safety and access to fun are top priorities!

Danielle affirms, “Local activities play a huge part in selecting a specific destination. Our family is quite active, and you’ll often find us enjoying the water or exploring the local terrain. Finding a property that is near to the activities we’ll be enjoying is huge. No one wants to spend a big part of their holiday in a car/bus/train.”

Danielle asserts, “There are occasional cases where we need to travel to a specific activity, but we weigh the pros and cons to determine which is the best property for us based on how we’ll be spending the majority of our time.”

Many families book vacations in rural areas with the desire to optimize health and wellness. That includes natural amenities like bodies of water, hiking trails, and waterfalls. 

Rick and his family can relate.

He maintains, “Activities shape the search. If water sports are the plan, then I want direct access. If hiking is the priority, I am looking for something within 10 minutes of the trailhead. The last thing I want is to spend half the trip driving just to get where I actually want to be. I have booked lake houses where you step out the door and onto a boat, and I have stayed in ‘nearby’ places that turned out to be 30 minutes from anything interesting. Those extra minutes add up fast.”

Tanya shares, “The vacation rental needs to be the type of neighborhood that seems clean and safe for my family. We like to exercise by walking or hiking to really take in the local area when I’m booking a vacation rental. If there are restaurants nearby, that can be a huge bonus.”

These days, Alice looks for kid-friendly amenities. That might mean a huge TV to stream movies on and also places they can connect in the great outdoors.

She adds, “I look for ‘walking distance‘ features like parks or a rental where we could easily hop on transit to get to places. If it’s the summer, ideally, the rental has a pool or is close to the beach or some kind of body of water where kids can splash around. I also book winter family getaways, and for these, I see if the place has sleds we can borrow, board games, or even a full games room.”

Tools For Finding Vacation Homes

“I often book private villas direct through their websites. The established properties can usually be found on multiple booking platforms (think AirBnB and VRBO) plus have their own website. I like being able to communicate more freely with the property management, making it especially easy to accommodate additional requests we may have in advance or anything that comes up during the stay.” – Danielle

“I use Airbnb and Vrbo, but I always check Google Maps before committing.” – Rick

“Generally Airbnb. I find VRBO’s interface isn’t as user-friendly. I also use Google Maps’ hotels feature, which shows vacation rentals in certain places (like Florida condos, for example). And these days, I’ll search via Perplexity or ask ChatGPT. But since ChatGPT has been known to come up with non-existent places, it’s a good idea to double-check its output.” – Alice

Tanya has been a loyal Airbnb customer for 15 years and uses Google Maps to sleuth (I love how she uses Google’s tools for virtually ‘walking’ the streets with Google Street View).

Red Flags at Vacation Homes

Better to know before you go, or book, for that matter!

One of the benefits of booking a vacation rental online is that you can find reviews from people who have stayed there before, including poor experiences.

“I will check multiple sources to find reviews on a listing such as Tripadvisor, Airbnb, and VRBO. A lack of reviews or poor photos is a red flag to me. I also look at what the host has replied to any negative reviews; it is telling about the host’s general demeanor when presented with negativity.” – Tanya

“If a listing claims to have ‘lake views,’ but the photos are all interior shots, that is a red flag. Sometimes a direct booking with a property manager gets a better deal, so I will dig around before locking anything in. The more research, the better,” Rick says.

What else deters Rick from staying somewhere?

He adds, “I don’t like it when the listing hides more than it shows. If every photo is a close-up of a coffee table but none show the full living room, there’s a reason. If multiple reviews mention ‘unexpected fees’ or ‘not as described,’ I’m out. And if there’s a long list of rules, like ‘No cooking strong-smelling foods’ or ‘No using the hot tub after 9 PM,’ that’s another bad sign. I don’t want to feel like I’m staying at a boarding school!”

Alice’s red flag is no reviews.

Additionally, she writes, “When the cleaning fee is exorbitant. Even if the price is reasonable, I’ll forego a place out of principle. Just include the cleaning fee.”

Choosing a Vacation Rental

The time has come to choose! After a long search for the perfect place to stay, it’s satisfying to move ahead with a booking to close the deal.

That said, there are so many beautiful places you could stay. How do you decide?

Danielle shares, “We typically aim for vacation homes or private villas because it’s much more comfortable as a family of four. Everyone has their own space to settle into, plus we’re able to prepare any meals or snacks that we may need during our adventures.”

What tips the scales for Danielle?

“Two major factors that will tip the scales on a certain property are the proximity to our desired activities AND if it has enough space. We aim to get the kids their own bedrooms, plus common space in the property is important for us all to hang out together and decompress from the adventures.”

Ultimately, Danielle will book a place if it meets all their non-negotiables, plus offers additional desirable factors, which vary based on the destination. She notes, “Sometimes it’s having a pool on-site, close to transit, chef and/or staff, etc.”

For Alice, the decision comes down to price and how quickly the host responds to her questions, citing, “I don’t want to stay at a place where I can’t get a hold of the host if there are problems.”

Continuing, Alice adds, “I generally research to compare pricing, but I’ll have a few places in mind and weigh where they are located with how close it is to amenities and how easy it is to get on transit if need be with what we plan on actually doing. If it’s a vacation where the vacation home is the vacation, then it’s all about the place. If it’s a vacation where the home is just where we sleep and eat, then location and proximity play a bigger role in my decision-making.”

What breaks a tie when choosing between properties for Tanya?

She exclaims, “If it comes down to deciding between two properties, I will compare the locations and prices and pick the best of the two. I will normally choose location over price as long as it’s not thousands of dollars more.”

Book Your Vacation Rental on Lake.com

When you want the home to be the vacation, there’s no better place to begin your journey than looking for a lake house on Lake! As Rick said, if you want to be on the water, be on the water. 

Discover lakefront homes and waterfront properties for short-term rental in Canada and the United States now on Lake.com.