You work from home. I work from home. Half the country works from home. And we all have the same problem: home is boring. Your desk is boring. The view of your neighbor's fence is boring. The only excitement in your work day is when the delivery driver rings the doorbell and your dog loses its mind for 45 seconds.
But here's the thing — your company said you can work from ANYWHERE. They didn't specify that "anywhere" had to be your spare bedroom. So what if "anywhere" was a resort suite in Orlando? Or a beachfront property in Myrtle Beach? Or a mountain lodge in Gatlinburg? Browse workcation-ready deals here and change your Zoom background from "virtual beach" to "actual beach."
1. The Workcation Math
Let me blow your mind with this calculation. You work from home Monday-Friday, 9-5. You do this from your house and spend $0 on vacation. OR you book a vacation deal for $99-$199, work from a resort suite Monday-Friday, 9-5, and spend your evenings and mornings at a pool, beach, or hot tub.
Your work output? Identical. Your happiness? Dramatically improved. Your vacation days used? Zero. ZERO. You worked your normal hours, just from a nicer location. This is the ultimate life hack for remote workers, and I genuinly can't believe more people don't do it.
| Category | Work From Home | Workcation Deal |
|---|---|---|
| Accommodation cost | $0 (you own/rent) | $99-$199 (3-5 nights) |
| Work productivity | Normal | Same or better |
| After-work activity | Netflix and laundry | Pool, beach, dining |
| PTO used | 0 days | 0 days |
| Happiness level | Baseline | Significantly elevated |
| Zoom background | Fake tropical scene | Actual tropical scene |
Pro Tip:
Schedule your timeshare presentation for a lunch break. Most presentations are 90 minutes, which fits perfectly in a long lunch. You attend the presentation from 11:30 AM to 1:00 PM, grab a sandwich, and you're back online by 1:30. Your coworkers on Slack will never know you "stepped away for a meeting" at a resort in Florida.
2. Essential Workcation Requirements
Before you book, make sure the resort can actually support remote work:
- WiFi speed: This is non-negotiable. You need reliable internet for video calls and file sharing. Call the resort and ask about WiFi speeds. Most modern timeshare resorts offer 25-50 Mbps, which is adequate for most remote work. If you need faster, bring a mobile hotspot as backup.
- Desk space: Most suites have a dining table that doubles as a workspace. Some newer resorts have actual desk areas. Check photos of the suite before booking.
- Quiet environment: You'll be on calls. Pools and hallways can be noisy. Work from the suite with the balcony door closed for important meetings.
- Power outlets: Bring a power strip. Resort suites were designed for vacationers, not remote workers. Outlet placement may not be ideal for a full work setup.
- Time zone: If you're traveling to a different time zone, factor that in. Working EST hours from a Mountain time zone resort means your workday ends at 3 PM local time — extra pool hours!
3. Best Workcation Destinations
The ideal workcation destination has good weather (for after-work enjoyment), reliable infrastructure (for during-work connectivity), and enough to do in the evenings:
| Destination | WiFi Reliabilty | After-Work Vibe | Deal Price |
|---|---|---|---|
| Orlando, FL | Excellent | Pools, dining, attractions | $79-$149 |
| Myrtle Beach, SC | Good | Beach, boardwalk, seafood | $79-$129 |
| Las Vegas, NV | Excellent | Shows, dining, nightlife | $89-$199 |
| Scottsdale, AZ | Good | Desert hikes, golf, spas | $129-$249 |
| San Antonio, TX | Good | Riverwalk, food, culture | $79-$129 |
4. Structuring Your Workcation Day
Here's my ideal workcation daily schedule (adapt to your work hours):
6:30 AM: Wake up, coffee on the balcony. Watch the sunrise. Remember that you're at a resort, not in your kitchen staring at the same wall you've stared at for 3 years.
7:00-7:45 AM: Morning swim or gym session at the resort fitness center. Get the endorphins flowing before work.
8:00 AM - 12:00 PM: Work block 1. Heavy focus work, meetings, emails. Sitting at the dining table with a view is objectively better than your home office.
12:00-1:30 PM: Lunch break. If the presentation is today, do it now. Otherwise, make lunch in the kitchen or grab something nearby.
1:30-5:00 PM: Work block 2. Afternoon meetings, wrap-up tasks. Light a candle, open the balcony for fresh air, and power through.
5:01 PM: Close laptop. Walk directly to pool. Do not pass Go. Do not collect $200. Collect a poolside drink instead.
Evening: Explore the area, try local restaurants, enjoy resort amenities, watch the sunset. This is the vacation part. And it happens every. Single. Evening.
5. Managing the Presentation During Work Hours
The timeshare presentation is the one scheduling challenge for workcation deal trips. Here are three approaches:
Option 1 — Lunch break presentation: Schedule it for 11:30 AM - 1:00 PM. Tell your team you have a "long lunch meeting." Technically true.
Option 2 — Light meeting day: Book the presentation for a day with fewer meetings. Block your calendar as "busy" for 2 hours. Handle the presentation and be back online within 2.5 hours.
Option 3 — PTO half-day: Take a half-day of PTO for the presentation morning. This is the most transparent option and ensures zero work stress during the presentation.
Fun Fact:
A study by Stanford found that remote workers who occasionally changed their work environment reported 13% higher productivity than those who worked from the same location every day. So technically, your workcation isn't slacking — it's a productivity optimization strategy. Put that in your performance review.
6. What to Tell Your Boss (and What NOT To)
This depends entirely on your company culture:
Chill company: "Hey, I'm working from a resort this week. Same hours, same output, different zip code." Most forward-thinking companies are totally fine with this.
Moderate company: "I'll be traveling for a few days but will maintain my normal work schedule remotely." Keep it vague. They don't need to know the details.
Strict company: Consider using PTO for a day or two and working the rest. Or just... don't mention the resort part. You're "working remotely from a different location." That's not a lie. It's just a selective truth.
What NOT to say: "I'm at a timeshare resort pool and logging into our video meeting in my swimsuit." Read the room. Or the Slack channel. You know what I mean.
7. Packing for Work and Play
Workcation packing requires dual-purpose planning:
- Laptop + charger (obviously)
- Phone hotspot capability (backup internet)
- Headphones with microphone (for calls without pool noise)
- A portable laptop stand or folded towel (ergonomics matter even on vacation)
- External mouse (optional but nice for long work days)
- Swimsuit, casual clothes, one nicer outfit for dinner
- Sunscreen for post-work pool sessions
The key is keeping it light. You're working and playing from the same location, so you don't need a full business wardrobe. Your coworkers only see you from the chest up on Zoom anyway. Business casual top, board shorts below the camera line. Classic workcation uniform.
8. Monthly Workcation Strategy
Here's the dream: one workcation deal per month. Twelve months, twelve different resorts, zero PTO used (or minimal). Your total accommodation cost for the year: $1,200-$2,400. That's $100-$200/month for a completely different work environment with resort amenities.
Compare that to a coworking space membership ($200-$500/month) that gives you a desk in a generic office. The resort gives you a desk PLUS a pool, PLUS a kitchen, PLUS a hot tub, PLUS a change of scenery. For less money. The coworking industry should be terrified of vacation deals.
Start building your workcation rotation at VacationDeals.to. Browse by destination and plan your monthly escapes from the home office monotony.
9. Workcation Tax Considerations
Quick note for the financially savvy: if you're working from a different state, there may be tax implications. Most states don't care about a 3-5 day work visit, but some (looking at you, New York) have aggressive nexus rules. If you're doing monthly workcations in different states, chat with a tax professional. This is not tax advice — I write about vacation deals, not tax code.
10. Your First Workcation Checklist
- Confirm your company allows remote work from different locations
- Choose a destination with reliable WiFi and within your time zone (or close)
- Book a deal on VacationDeals.to
- Block your calendar for the presentation day
- Pack your work essentials + vacation essentials
- Test the resort WiFi immediately upon arrival (have hotspot backup ready)
- Set up your workspace at the suite dining table
- Work your normal hours, then close the laptop and live your best life
- Repeat monthly until retirement
The remote work revolution gave us freedom from the office. Vacation deals give us freedom from home. Combine them and you've cracked the code to a life where every week includes a little bit of paradise. Your commute is now the walk from the bed to the balcony. Not bad for a Monday morning.
Pro Tip:
If you're on a workcation and have a video meeting, position yourself so the resort background is visible but not distracting. A subtle palm tree or pool in the background generates way more jealousy than any virtual background ever could. When someone inevitably asks "wait, where are you?", just smile and say "working remotely." Power move. Visit our brand page to find resorts with the best work setups.