Working Remotely in Orlando


A) We live in NJ and like to spend time in Florida from Jan-Mar to escape cold.
B) Looking to rent a 2BR+ place by the month, for 1-2 months, budget $5k/month.
C) Ideally has a desk/ergonomic chair, but at minimum a kitchen table & chair to work on.
D) Looking for something that has things nearby you can walk to. Stores, green spaces, activities, etc.
E) Short Uber or shuttle ride to WDW/UOR. Will probably not have a car.

Questions for Liners:

  1. What greater Orlando neighborhoods should I consider?
  2. Any suggestions on places to stay? Not opposed to staying at WDW/UOR hotels if it meets our other requirements.
  3. Anybody worked remotely in Orlando for an extended period of time? How did you do it?

Edit: this is mainly just DW and me - 2 people - although DD’s & their SO’s may visit.


Paging @Bubblez


Good call :rofl:


I’ve done a ton of research for this!

I went on VRBO with an emphasis on places near WDW. I found Reunion resort which we’re using for all of this coming Dec-January to escape the Vegas winter.

Some rentals include full access to all of the country club amenities including full golf privileges and access to all eateries and water parks.

There is a shuttle to get to WDW but I’m seeing advance notice is required for that perk.

We found a super cute house right on the golf course with a full in-law quarters for DS. They converted the 2 story garage to a full arcade and apartment. DH gets his view and his space for work, I get Orlando, DS gets privacy and full access to any club activities. It’s a win win all around.

There are also condos closer to the bubble, by Disney Springs that was better in proximity that could also work, but we needed more space.


My downside to that is a friend stayed down there and said with the traffic on 4 it can make getting to and from the parks challenging. But we’d be coming and going at odd hours so it won’t affect us much.


We are using this as a test run to see if we like that area. If we do we’ll look into buying a condo or smaller house which we’ll only use for those winter escapes, but filled with out creature comforts like our own beds or special coffee makers.


#3, we worked from the hotel rooms at both Bay Lake and Beach Club. It was actually very easy. But expensive.

I’d recommend starting at something cheaper to start, especially if looking longer term. $800 a night x3 adds up after 60 days. :roll_eyes:

We asked the front desk if they could find a more comfortable chair for DH so he could work mornings. We ended up buying one on Amazon and store it with the Owner’s Locker people, along with the 3 monitors he also had to buy.

After he was set up, he’d work until he could join me for lunch in the park. Then he’d go back (we were working on west coast time) work some more and nap, then he’d meet me for a late dinner and date nights at whatever park we wanted.

It was the absolute best, especially when we were at Beach Club and the park was right outside.

Highly, highly recommend.

You can Instacart from Best Buy whatever electronics you’d be missing, or use Amazon. We did both. And like I said, we’re storing an office chair, 3 monitors and 4 “tubs” of stuff with Owners Locker who will store everything until we get back, then they drop off/pickup as needed.


I was going to tag her too :rofl: :rofl:


@Bubblez Thanks for this valuable info!

Owner’s Locker sounds like the shizzle to store gear in Orlando and retrieve it when you come down. Although, your husband out-geeks me - I only have 2 external monitors :nerd_face:

You have winter in Vegas?? Maybe at night, I suppose :sunglasses:
Still, Orlando is a nicer place to be in winter than either Vegas or NJ :slight_smile:

What does that run per month, if you don’t mind my asking?


For us, all in for 2 months is just over 20K. But that’s catered to our needs and Reunion is filled with most price points.

I used VRBO, and just dong a quick search I was able to find several condos/townhomes within your requested budget, though not with the included resort access outside of normal pool usage. I was going to link a few here but the link was very wonky looking. Not sure if the new website supports links like the old one did.

When looking on a map, here is Reunion in yellow. The other houses fit your requirements but for a Jan-Feb stay.


My DH grew up outside of Chicago. He ran away from the cold 20+ years ago, and never stopped. Winters in South Florida are our favorites, because even Orlando can get a little chilly for him! But yes, it can drop into the 20’s and 30’s in Vegas which is too cold for him anymore. (He used to live in NJ back in his post grad days)

Your link worked! I wonder why mine was being wonky. Operator error, probably.

2 is still impressive. But yes, he usually out geeks everyone. He built a very successful data analytics company while I was dragging him all over Disney. He kind of has to out geek everyone. :blush:


We might be getting a storage unit instead of the lockers. I forgot they wouldn’t take the chair, which was why we tried to have them deliver one. We ended up donating the two chairs we had to buy to Mousekeeping/maintenance. But they for sure store monitors.

Most hotels/rentals have normal chairs, but he needed a high back plush chair for his back while coding.


Thanks, I’ll have a look!

We are quite similar :smile:

We’re from Canada originally so know how to cope with winter but really don’t want to. It’s why we left, eh :cold_face:

Any idea on where in South Florida to work remotely that might fit our requirements? We like Greater Miami :sunrise:

Thanks for clarifying, I was wondering about the chair aspect.


My Doctor is in North Beach, and we’re going to see him before we take the new train up to Orlando. We really like Plantation and Davie in Broward County, it had the laid back, suburban feel. But thats more of a “moving too” vibe. Naples has piqued our interest, but not enough to stay more than a few nights in a hotel by the beach.

Hollywood might have some great condos on the beach too, now that I think of it. If we didn’t need the land for our kids, we would have absolutely done a condo there. That’s be great for “relocation, not vacation” wintering!

And I forgot you were in Canada before! 30 might feel like a nice day for shorts for you!

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Well, the main thing is I get to wear shorts when working remotely :sunglasses:


I work remotely but I’m not allowed to work “remotely “ …as in outside my province. Except in extenuating circumstances… like catching Covid and not being allowed back in the country.

I wish I could work from a warmer climate in winter.


The irony!

I’d like to work remotely in Montreal (my hometown) in summer, but company rules require me to work in the US :cry:

One idea I had was work out of Plattsburgh, NY or Burlington, VT and drive to Montreal for weekends/days off.


Or even train?


as in, rail travel between Montreal and the US?

Thanks for raising - just found out that the Amtrak Adirondack has recently resumed service to Montreal, although it’s no speed demon - 3 hours or more to Plattsburgh. It had been suspended the last few months over concerns about safe track conditions in the summer heat.

The Amtrak Vermonter currently terminates in St Albans, VT. Prior to '95 it ran to Montreal and was known as the Montrealer. The Vermont Congressional delegation are pressing to restore service to Montreal; I hope they’re successful. I like trains :bullettrain_side:

Meanwhile Adirondack Trailways has extended bus service to Montreal from Plattsburgh - I took it once and was pleased, so that could be a good option for those who prefer not to drive.


Thanks for the Amtrak update. I knew it had gone to Montreal at one time.

Your mention of living in Plattsburgh to weekend in Montreal prompted the Amtrak thought.

Tho I doubted it was a thing.

If we want to talk about lessons learned from 9/11, reliance on rail travel should be one of them.

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