Short-Term Rental Operations Virtual Assistant

Bookings Shouldn’t Break Between Stays

Reservations stay aligned across calendars without you double-checking
One person owns bookings, turnovers, and guest coordination end-to-end
Stays don’t stall between check-out and check-in or come back incomplete

No more checking if the next stay is actually ready

4.8/5 avg.

Leader in Managed Virtual Assistant Services

2M+ applicants screened annually
10,000+ companies supported
20+ countries

10,000+ Active Assistants Powering 10,000+ Companies

What Wing Assistants Get Done Every Day

Bookings confirmed and synced across platforms. No calendar mismatches across listings.

Updated across booking platforms

Same-day turnover scheduled and confirmed with cleaners. No gaps between check-out and check-in.

Coordinated with cleaner + calendar

Guest messages handled before arrival. No missing check-in details or unanswered questions.

Replied in platform inbox

Upcoming stays reviewed for readiness. No surprises with access or unit status.

Checked in PMS + calendar

Your Short-Term Rental Operations Virtual Assistant Handles

Booking Coordination

Confirm new reservations
Sync bookings across platforms
Track booking changes

Calendar Management

Update availability calendars
Prevent double bookings
Keep calendars aligned

Guest Communication

Respond to guest messages
Send check-in instructions
Handle booking questions

Turnover Scheduling

Schedule cleaning between stays
Confirm cleaner availability
Prevent turnover gaps

Listing Updates

Update listing details
Keep platform info aligned
Apply content changes

Stay Readiness

Check upcoming reservations
Flag readiness issues
Confirm check-in details

How it Works

Be as involved (or uninvolved) as you prefer – our expert recruiters will guide you through every step, ensuring a smooth and seamless experience.

Step 1

Meet us to discuss
your requirements

Step 2

We shortlist talents
for your review

Step 3

We interview and
assess candidates

Step 4

The perfect Wing Assistant joins your team

Measured Results Across Teams

Real companies. Defined ownership. Measurable outcomes.

Quistem

Needed executive ops owned.

25% CEO time reclaimed
9 workflows offloaded
1,000+ days supported

Cybersecurity Startup

Needed outbound sales owned.

2,080+ hours delivered
22 sales workflows owned
Sales system live (2 wks)

Provida Family Medicine

Needed clinic ops streamlined.

50% faster admin ops
35% fewer billing errors
25% faster claims

Idaho Legal Estates

Needed intake owned.

100+ hours reclaimed
13+ hours saved weekly
10 workflows fully owned

My Personal Mentors

Needed revenue stabilized.

30+ deals closed monthly
3,600+ clients supported
48-hr inquiry resolution

Delegate Everything but Leadership.

More Virtual Assistant Services

We offer 25+ distinct plans in sales, marketing, customer service, and other operational areas. We also have dedicated industry-focused services such as Real Estate Assistants, Healthcare Virtual Assistants and E-Commerce Virtual Assistants.

Speak to a Wing Expert and find the right fit for your business.

Executive Assistant

Discover expert-tier talent to help with presentations, proposals and more

Sales Development Rep

Engages with prospects, grows your sales pipeline and drives sales

Personal Assistant

Manages your calendar both at work and outside of it

Real Estate Assistant

All-round help for your property listings

Top 1% of Talent

Start in one function, then expand coverage as the business grows.

Healthcare Assistant

Helps co-ordinate appointments with patients, data-entry and insurance filing

Digital Marketing VA

Discover experts in ppc ads, email marketing and growth

Bookkeeping Assistant

Tracks expenses, maintain your books and reconcile statements

Customer Service Rep

Delivers customer support for general queries, complaints and feedbacks

Bookings Break When Calendars and Turnovers Don’t Align

You can’t stay on bookings, guest messages, and turnovers all day. But check-ins still depend on everything lining up.

Your Wing Virtual Assistant works inside your listings and calendars and stays on updates until bookings, turnovers, and guest details are aligned.

How Wing Keeps Rental Operations Moving

This isn’t shared coverage or reactive support—one virtual assistant stays on your bookings, calendars, and turnovers, backed by support, so updates don’t stall or need to be checked again.

Flexible, No-Commitment Monthly Support

Add support when booking volume increases or turnovers stack up. Scale back when things stabilize without changing how operations are handled.

NDAs and System-Level Access Control

Your assistant works inside your tools with defined permissions. You control what gets accessed, updated, and shared across listings and systems.

Secure and Compliance-Ready

Wing is SOC 2–certified and HIPAA-compliant. Data is encrypted in transit and at rest, with restricted and logged access.

Coverage That Doesn’t Break Between Stays

One assistant stays on your bookings and turnovers day to day. If coverage expands, updates continue without re-explaining or catching anything back up.

We Meet Challenging Talent Needs and Ensure Ongoing Success

Our resources and systems are designed to deliver tailored solutions that go beyond the basics, empowering your business to thrive.

Customer Success Manager

Benefit from a dedicated Client Success Manager (CSM) who will be your single point of contact for all your needs. Your CSM will ensure smooth onboarding, provide ongoing support, and proactively address any concerns to maximize the value of our services.

Free Replacements

We can work with you to analyze your requirements, and can launch new recruitment processes/ roles exclusively tailored to your needs, in your budget.

Quality Control & Supervision

Your assistant isn't alone. They're supervised by both Wing's Team Captains and Supervisors.

Additionally, you can opt-in to use sophisticated artificial intelligence technology that flags potential issues ahead of time to our supervisory team, who work to proactively resolve issues.

If quality is your goal, Wing remains the best choice in this industry.

Custom Roles

We can work with you to analyze your requirements, and can launch new recruitment processes/ roles exclusively tailored to your needs, in your budget.

Operational Ownership, Powered by the Wing Workspace App

Wing doesn’t just assign an assistant. We run execution through a centralized, human + AI–powered workspace built to keep work moving around the clock.

Real-time task visibility and status tracking
Documented workflows with built-in oversight
Structured handoffs and cross-time-zone continuity

Highly Rated by Operations & Leadership Teams

4.5

123 Reviews on Google

4.7

51 Reviews on Capterra

4.8

10 Reviews on Goodfirms

4.8

18 Reviews on Clutch

Hundreds of Stellar Client Reviews

Overall, I have been very pleased with each aspect of hiring my Wing VA. We were looking at a variety of virtual assistant programs; what made us choose Wing was the fact that their talent had specific marketing experience... Working with Wing is seamless. They have a robust platform that makes communicating with our VA incredibly easy. It also helps that they act quickly and are incredibly responsive...

Christine Mulvey

Director of Marketing
charlesgate.com

I've had the best VA experience so far after multiple tries. The app is easy to use to communicate and create tasks, there's loads of real-person communication, and my assistant was so capable at MANY things. He was so good that every week I found more things I could take off my plate and all for a low fixed price per month. Great value and it's taken a lot of stress off me.

Kelsey Galarza

Co-founder, Orange Marketing orangemarketing.com

Amazing service! Excellent customer support and the work done by my assistant Kirti S. from Wing is top notch. I’ve enjoyed the help and the genuine personality and willingness to learn. Also a big call out to Maryann U. my customer success manager. She is fantastic and so full of life.

Chris Mullaly

Founder and Managing Partner spiruscapitalpartners.com

Wing is an innovative software-powered interface to virtual assistants. Wing has provided a software-augmented virtual assistant service that's unique in the field. Just as important as the software platform is the quality of their assistants behind the scene. Their ability to organize and run a process of matching our needs with available talent was successful. Wing is easy to use.

Roy Chua

Principal AvidThink avidthink.com

Wing provides exceptional Virtual Assistant services and an accompanying productivity platform. Using Wing has been incredibly beneficial for our business, allowing us to explore some things in far more depth, or scale up some operations more effectively. Some of the benefits far exceed what you might expect from a virtual assistant in terms of capabilities and outside traditional administrative work.

Dylan Schiemann

Co-Founder &CEO
livingspec.com

What I like best about Wing is the quality and reliability of their virtual assistants. We started with one assistant and were so happy with the experience that we’ve since onboarded additional VAs. I’ve also confidently recommended Wing to colleagues and contacts looking for virtual assistant services. The combination of strong support, trustworthy assistants, and a seamless experience is what sets Wing apart for me.

Marysa C.

Mid-Market (51-1000 emp.)

Short-Term Rental Operations Virtual Assistant Pricing

Choose part-time or full-time. Bilingual support is available if needed.

Either way, one person stays responsible for your work, and nothing sits waiting or comes back half-done.

Need help?

Book a Meeting

Book anytime this week

Live Chat

6-9 PM PST weekdays

Full-Time

16% Savings

$1,099/Month

160 Hours per month
Dedicated Short-Term Rental Ops VA
Free replacement
Customer Success Manager
Rigorous quality control and supervision
Wing Workspace App
Your timezone—any hours you want
Share with colleagues
Unlimited file sharing/storage

Part-Time

$550/Month

80 Hours per month
Dedicated Short-Term Rental Ops VA
Free replacement
Customer Success Manager
Rigorous quality control and supervision
Wing Workspace App
Your timezone—choose from designated slots

Sharing is limited
10 GB file sharing/storage limit

Bookings Shouldn’t Break Between Stays

What Wing Assistants Get Done Every Day

Your Short-Term Rental Operations Virtual Assistant Handles

Booking Coordination

Calendar Management

Guest Communication

Turnover Scheduling

Listing Updates

Stay Readiness

How it Works

Meet us to discuss your requirements

We shortlist talents for your review

We interview and assess candidates

The perfect Wing Assistant joins your team

Measured Results Across Teams

Quistem

Needed executive ops owned.

Cybersecurity Startup

Needed outbound sales owned.

Provida Family Medicine

Needed clinic ops streamlined.

Idaho Legal Estates

Needed intake owned.

My Personal Mentors

Needed revenue stabilized.

Delegate Everything but Leadership.

More Virtual Assistant Services

Bookings Break When Calendars and Turnovers Don’t Align

How Wing Keeps Rental Operations Moving

Flexible, No-Commitment Monthly Support

NDAs and System-Level Access Control

Secure and Compliance-Ready

Coverage That Doesn’t Break Between Stays

We Meet Challenging Talent Needs and Ensure Ongoing Success

Operational Ownership, Powered by the Wing Workspace App

Get it on

Get it on

Get it on

Highly Rated by Operations & Leadership Teams

4.5

4.7

4.8

4.8

Hundreds of Stellar Client Reviews

Short-Term Rental Operations Virtual Assistant Pricing

Live Chat

$1,099/Month

$550/Month

Popular Questions

Wing Assistant2150 Shattuck Ave,Berkeley, CA 94704

251 Little Falls Drive, Wilmington, DE 19808

We're Hiring

Digital Marketing Assistant

Virtual Assistant

Customer Service Reps

+ Many other positions!

Meet us to discuss
your requirements

We shortlist talents
for your review

We interview and
assess candidates

Wing Assistant
2150 Shattuck Ave,
Berkeley, CA 94704

251 Little Falls Drive,
Wilmington, DE 19808