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We Did It! Put Deposit on One-Month Vacation Rental

My family just got back from a 12-day trip to California and Colorado that involved trains, planes, Ubers, streetcars, cable cars and buses. It was exhausting, and I’m so glad to be back home!

Which is why it’s weird that the first day I returned home, I was already planning next summer’s vacation. Why? I wanted to reserve a vacation home for an entire month, and next summer’s dates were already starting to get booked.

Can We Relocate for One Month?

Some of you may remember that last fall, I pondered (as I mowed the lawn) the idea of spending an entire month in one location over the summer. My husband and I could both work remotely, and this would give us the chance to explore one area in depth and discover some local treasures. Since we already had two big trips planned this summer, the idea would have to wait until at least the summer of 2018.

My husband and I actually forgot about the concept of a long-term summer vacation rental until our kids brought it up last month. They never forget!

So, we thought about the idea more seriously. And honestly, nobody would miss us here for a month. We don’t have family nearby. Many of our kids’ friends go away on their own trips or stay with their grandparents over the summer.

We could take our dog or board her. Our kids would still have over a month after we returned to spend in our hometown. So why not take the plunge?

I realized that if we were going to seriously entertain the idea of renting a place for a month, I needed to get busy searching for that perfect place ASAP.

Deciding on a Geographical Location

First things first: we had to decide where we most wanted to spend an entire month. We had lots of ideas.

First and foremost, we wanted a location with an interesting “backyard” or scenery at our doorstep. Since we can’t spend big money on entertainment for an entire month straight, we need the location to provide some free visual entertainment. This could be a house in the mountains, an apartment in a big city or somewhere near a lake or the ocean. We do not want to rent a house in suburbia similar to where we currently live.

Ideally, we also want to rent a place where it wouldn’t be necessary to rent a car for the entire month. I want to be close to restaurants, a grocery store and/or public transportation.

It wasn’t hard for my husband and I to agree on the location. We didn’t even ask our kids, because we know they would wholeheartedly agree.

However, we decided not to tell our kids just yet. It’s too far away, and I don’t want to hear about it from them for the next 10 months. So, in order to prevent someone from accidentally spilling the beans to our kids, I won’t be revealing the location on Miles For Family just yet.

We Did It Put Deposit Down on One-Month Vacation Rental

Is it here?

We Did It Put Deposit Down on One-Month Vacation Rental

Somewhere with a view like this?

We Did It Put Deposit Down on One-Month Vacation Rental

What if this was our backyard?

Priority Features of a Rental Home

Now that we chose the location, it was time to find the right rental. What features were most important? What could we live without? I made a mental list of priorities.

Pool. My kids spend such a large percentage of their summer swimming that I knew we had to have access to a pool with our rental. We don’t necessarily need a private pool (although that would be awesome!), but access to a neighborhood or condo building community pool is a must. A hot tub would be bonus, but not a requirement since we don’t have access to one now.

Space. We just spent the last 11 nights crammed into hotel rooms with all of us sharing beds and sleeping in the same room. By the end of our trip, we were all getting on each other’s nerves. I know that we won’t survive an entire month sleeping in the same room. I would like everyone to have their own bed. We could work with three bedrooms or two bedrooms plus a sofabed.

Location. On shorter trips, I’m willing to stay farther out and commute in for the action. But if we’re committing to a place for a month, I want the location to be more central. As I mentioned above, it has to be convenient to scenery, stores and restaurants.

WiFi. Of course, the place also needs to have good WiFi so that my husband and I can work remotely. Most places nowadays do, except from experience the connection in more remote places is spotty.

Searching for a Rental

Looking at all the rental options was the most fun part of this process! I could look at house rentals all day and dream about staying in different homes.

I looked at Airbnb, vrbo/HomeAway and craigslist. Also, I Googled “vacation rentals” and the name of the city and found some real estate pages that offered monthly vacation rentals. I have rented from vrbo in the past, so I was most familiar with that site.

Honestly, the number of rentals in our desired location and price was just overwhelming. It’s good to have choices! I bookmarked a few to return to, but sometimes when I went back to them, part of our dates had already been booked. I must decide quickly!

The filters on these sites are pretty good, but I had to adjust the price filter. I was looking to pay no more than $100/night, but since many places offer discounted rates for longer-term rentals, I had to increase the price per night to account for that adjustment.

As I was perusing the vacation rentals advertised on craigslist, I noticed that many of them listed rentalo.com at the bottom. I hadn’t heard of this site, so I decided to check it out.

The idea behind rentalo seemed great. Just input the city, number of people and dates for your desired rental and owners would contact you via email with offers. I decided to try it.

Unfortunately, I only got three responses. They were all priced much higher than similar condos in the area listed on the other sites. So, rentalo.com was a bust for me.

Deciding on “The One”

I went back to HomeAway. Since there were plenty of options, I started to dig really deep into each rental. Did it have carpet or hardwood/tile? (I’m a little worried my kids will spill something on carpet).

For the listings that revealed the name of the condo building, I looked at the locations on Google Maps. What things were right next door?

I read lots of reviews. For my top choices, I also read reviews of other rentals in the same buildings to make sure that people liked the condo complex in general.

I narrowed the choices down to about five. A few of them wanted all of the money up front, which I was not ready to do.  So I focused on ones that had a smaller upfront deposit.

After exchanging a few messages through Homeaway and communicating through text and a quick phone call, I made my choice and signed a rental agreement. I had just committed to a four-week vacation rental!

Fears and Risks

I’m NOT worried about being scammed out of money or that the place will be a dump. I paid through HomeAway and PayPal, so I would get my money back.

My biggest worry with a four-week rental is that the owner will back out at the last minute and we won’t have a place to stay. One of our weeks falls over the July 4th holiday, and places are sure to be sold out that week. I would imagine that finding a place that is available for four weeks in a row at the last minute would be challenging.

I talked to my friend whose husband works for the HomeAway corporate office, and she put my mind at ease. Her family has used HomeAway for rentals in the past, and they have never had an issue with the owner canceling last minute. She said that most owners depend on rental income and a good reputation with sites like HomeAway, so they don’t want to mess up that relationship.

HomeAway offers payment protection and emergency rebooking assistance. I hope I don’t have to use either one!

Of course, I wonder if my kids will be too loud and fight too much in our rental, and if they will break something. Will we get homesick?

However, I believe the rewards of this experience will outweigh the risks. This will be something we will always remember, and we don’t have many more years to do it. The days are slow, but the years are flying by!

Miles and Points

For this rental, I’m not using miles and points. We will be saving up cash. Unfortunately, vrbo and HomeAway are not coded as “travel” for miles and points travel rewards cards like the Capital One Venture Card and the Barclaycard Arrival Plus. However, if I had Amex Membership Reward points, I could use them to book Airbnb properties.

Even though this vacation won’t be a traditional miles and points “free” trip, we hope to use airline miles to get to our destination. Also, we are considering using Hilton points to stay at a resort for a few days prior to the start of our rental time.

Have you ever rented a vacation home for an extended period of time? I’d love to hear your experiences!

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Author: Nancy

Nancy is a contributing writer for Miles For Family. She enjoys traveling to the beach and is a big fan of Disney. Nancy lives near Dallas, Texas, with her husband and three kids.

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28 thoughts on “We Did It! Put Deposit on One-Month Vacation Rental

  1. Congrats on booking an extended vacation! My family only vacations for one week tops, and you can’t really relax when you are trying to cram as much as possible into a short time period. A month-long vacation sounds amazing.

    • @Sam I will do a separate post on the place we are going sometime. My kids start school in a few weeks, and I know that once they get into the school year they will need a pick-me-up with some good news about a future vacation. 🙂

  2. After retiring, for three years in a row my wife and I took month long trips around Europe. The following year we decided to find a place to just sit on an Atlantic ocean beach for a month. My wife identified a great property in an area new to us on Home Away. After arriving, we found our way around quickly and met some locals who became fast friends. We booked the property again 6 months later and after that trip the place seemed like a second home. Now after 8 years of returning to the same house twice a year we feel like locals ourselves. We have many friends there and even welcome newcomers to the area. I think you will find the feeling of belonging is the best part of staying somewhere for a month. Enjoy!

    • @bnabill That sounds amazing! I’m glad you found a place that was so welcoming! My family has been to the area we picked before, and we fell in love with it. I’m already wondering in my head if we will repeat the experience again after next summer.

  3. A month with a beach view would be my happy place (I’m not a mountain person). We just returned from Maui & Kauai and we booked via VRBO 2 condos. I loved having a bedroom, full kitchen, multiple bathrooms, and a washer & dryer. It just makes my life so much easier with meals, and hubby and I can relax after sightseeing or being at the beach/pool all day with the kids.

    I can’t wait to hear where you guys are going.

    • This was my 3rd time to Maui and 1st time to Kauai. I actually prefer Maui because of the restaurants, Whalers Village, and Lahaina Front Street, and I like staying in Kaanapali (Hyatt, Hyatt Residence, and Honua Kai – we’ve stayed at all of them in the past few years).

      As for Kauai, it feels like you’re in Jurassic Park, and it’s absolutely beautiful. We stayed 3 days in Kapaa (mid-island @ Waipouli Beach Resort) and 3 days in Poipu (South Beach) @ Grand Hyatt Kauai. We did a boat excursion on the Napali Coast and went in the sea caves (my kids loved it) and we snorkeled at Lydgate Beach.

      I’m actually researching Kona (Big Island) for another summer trip for a week and then a few days on Oahu (Pearl Harbor and some sightseeing) as I want to experience all of the islands.

      My family did make it very clear to me that they’re all dying to go to WDW so somehow I need to make that happen. I’m trying to do one sightseeing trip and one relaxing trip per year, and WDW does not fall under relaxing to me 🙂 unless I can squeeze in a DL cruise somehow.

      • How do you like the Grand Hyatt Kauai? We are headed there as a family of 4 for 5 nights next year. We’ll have a 9 and 6 yr old so I think the pool complex will be great, but the rooms may be tight.

      • @Stephanie Your trip sounds amazing! We are hoping to stay at Waipouli Beach Resort also, but I haven’t booked it yet. I’m afraid after our trip to Hawaii next year I will also want to see the other islands (Maui and the big island).

        WDW is definitely not relaxing for me either!

      • @Cheapblackdad – we were super impressed with the Grand Hyatt Kauai grounds, but not the room itself – it’s outdated and simple, double sinks, bath/shower, fridge and 2 queen beds with a lanai – our view was of the garden and partial ocean view. However, the pools, saltwater lagoon and beach are just beautiful and so much fun. It’s a huge resort so be prepared to walk 10 – 15 min to the pools. We didn’t swim at their beach as it was a little rough, but for snorkeling, there’s Poipu beach next door or Lydgate which is a 20 min drive.

        Since I booked with points, they waived the $35 resort fee which includes parking and free self service laundry & detergent amongst a few other things. I was also able to use my Lounge Certficate, and we loved their breakfast, evening appetizers, and dessert spreads. The food at the pool and their restaurants are the most expensive I have seen at any Hyatt.

        I recommend seeing the Napali Coast by boat and take a drive to Waimea Canyon. They are both stunning

      • @ommax it’s funny that we have absolutely no interest to stay at Aulani. I would rather put that money towards DCL and have food included. My kids have been watching WDW rides on youtube and are making a mental note of what they want to ride.

  4. I read some posts about people taking longer vacations with their family, and one of the tricks to it is doing bulk cooking beforehand or once a week, so you don’t feel like you’re working quite so much on your vacation. Good luck and have fun!

    • @Leana I’m not sure how long I can keep the secret from my kids. I’m about to burst! I’m obsessed with looking at photos of the rental, especially the view from the master bedroom. I will be crushed if this rental falls through!

  5. A year and a half ago, my family did a 5-week rental vacation in Cancun. We stayed from the beginning of December until a week into January — to avoid paying high airfare for the busy holiday season. Doing Christmas in MX was an adventure for us. Our apartment’s backyard was the beach (with palm trees), and it was amazing. I worked remotely part-time.

    By staying for a longer period, we were able to do adventurous activities far more cheaply than we could have in a quick 1-week vacation. This was mainly because we never had pressure to do a specific activity right now — it could wait until the next day or the next week if the price was too high. We also discovered many off-the-beaten-path attractions.

    Regardless of where you are going, it will be a great break. A month is plenty of time to reset and feel fresh when you return home.

    • @Dave Your time in Cancun sounds amazing! Spending the holiday season at the beach in Mexico would be so lovely. My kids will be 7, 10 and 14 by the time next summer rolls around. I’m looking forward to doing a few adventurous things with them.

  6. Sounds awesome. I have to say I did have a couple last minute cancellations before. I guess you need to look at the reviews and also talk with the owner to assess that possibility. I wish Homeaway had the same penalties on owners than on renters!

  7. This is so cool! I love it. The key is having a role both parents can do virtually from anywhere. If you have that, you’ve got options.

    Super excited for the big reveal.

    Now I’m thinking about where our family would want to spend a whole month.

    • @Cheapblackdad My husband can’t work remotely all the time, but he thinks he can do it temporarily. He doesn’t live and work in the same city as most of his co-workers anyway.

      I know my kids will be excited when we tell them, but I’m afraid when I reveal it on here people will be scratching their heads. It’s probably not the most popular destination.

      It’s fun to dream about potential long-term vacation locations!

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