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Getting Started with Nest Stays: A Property Owner's Roadmap

Nest Stays ·
Getting Started with Nest Stays: A Property Owner's Roadmap

Most property management company websites will tell you what they do. Very few will tell you how it actually starts: what the first few weeks look like, what they’ll ask of you, when you can realistically expect your first booking, and what the ongoing relationship looks like once the property is live.

That’s what this is.

If you own a property in Costa Rica and you’re seriously thinking about professional management: not just wondering whether it’s worth it, but actually trying to understand how it works: here’s the real roadmap.


The 5-Step Onboarding Roadmap

Step 1: The Intro Call

Everything starts with a 30-minute call. No pitch deck, no pressure, no prepared script about why professional management is life-changing.

The call is a conversation. We want to know about your property, where it is, what condition it’s in, how often you use it, what you’ve tried before. You want to know whether we can actually move the needle on your income and whether we’re people you’d trust with your home. Both things get answered on that call.

You’ll know pretty quickly whether it’s a fit. Some owners are ready to move forward by the end of the call. Others have questions that need answers first: about their specific location, their existing setup on Airbnb, or concerns about a renovation they’ve been meaning to do. That’s all fine. The call exists to give you the information you need to make a decision, not to close a deal.

→ Schedule your 30-minute intro call at cal.com/neststays/intro


Step 2: Property Assessment

After the intro call, we take a real look at your property: location, condition, current occupancy (if you’re already renting), and what we think it can realistically earn under professional management.

This is where we’ll be honest with you. If your property needs work before it’s guest-ready, a fresh coat of paint, updated bedding, a proper photography shoot: we’ll tell you. If there are structural issues that would complicate management, we’ll tell you that too. We’re not going to sign you up and then surface problems two months later.

We’ll also give you an income projection based on comparable properties. Not a rosy estimate designed to get you to sign, a realistic range based on your property type, location, and availability. For specific income figures by property type and what actually drives your number up or down, read our guide to rental income at Los Sueños. If you’re comparing vacation rental income to long-term rental options, our guide on Airbnb vs long-term rental in Costa Rica breaks down the real numbers and tradeoffs.

The assessment covers:

  • Location factors: view, proximity to amenities, accessibility
  • Property condition: what’s guest-ready, what needs attention
  • Competitive positioning: how your property compares to active rentals in the same area
  • Projected income range: realistic annual figures, by scenario

Step 3: Onboarding

This is the production phase. It typically takes 2–3 weeks and covers everything needed to get your property live and performing.

Photography. We coordinate professional photography at no cost to you. Good photos aren’t a nice-to-have: they’re the single biggest driver of first-click conversion on Airbnb and Vrbo. We’ve seen identical floor plans where the professionally photographed unit earns 40% more. The shoot is scheduled around your timeline.

Listing creation. We write the descriptions across all platforms. Not a generic list of amenities, a narrative that makes someone choose your property over the one next door. We list on Airbnb, Vrbo, Booking.com, and DirectStays (our direct booking channel). Different guests use different platforms; we’re everywhere they look.

Dynamic pricing setup. Your rates are managed by market-responsive pricing software, calibrated to local seasonality, tournament calendars, occupancy pace, and competitor availability. Rates adjust automatically: not set-and-forget, but actively managed.

Cleaning team introduction. Your dedicated cleaning crew is briefed on your property’s specifics: how things are organized, what needs special attention, your standards for presentation. They work from a consistent checklist every turnover.

Your preferences, documented. Owner blackout dates logged. House rules established. Emergency contacts registered. Maintenance thresholds set (how we escalate, what we handle in-house vs. what we flag for your approval).

By the end of onboarding, your property has a complete operational file. Everyone who touches it knows how it runs.

The reason every detail in this process matters: better-presented properties attract better guests, and better guests leave five-star reviews that drive the next booking at a higher rate. That’s not marketing copy. It’s the actual mechanism behind properties that consistently earn at the top of their range rather than the middle.


Step 4: First Guests

Listings typically go live within 4 weeks of your first call. For most new listings on established platforms, the first booking arrives within 2–4 weeks of going live: though this varies by property type, location, and time of year. Realistically, count on 6–8 weeks from start to first guest.

Here’s what that looks like in practice:

The first booking notification. You’ll get an alert when it comes in: property, dates, guest profile, rate. You don’t need to do anything; we handle the confirmation and all communication with the guest.

The first guest check-in. We manage arrival coordination, send the property guide, handle any questions. If something comes up (a light bulb out, a question about the WiFi) we handle it before it becomes a review issue.

The first guest review. This matters. The first few reviews establish your listing’s trajectory on Airbnb’s algorithm. We actively follow up with guests to encourage feedback, and we respond to every review. One five-star review that mentions the concierge experience or the view or how smoothly check-in went carries more weight than any listing optimization.

Your first monthly report. At the end of the month, you get a full breakdown: bookings, gross revenue, Nest Stays’ 25% commission, cleaning fees, any expenses, and your net payout. Same format every month, no surprises.


Step 5: Ongoing Management

Once the property is live, the work doesn’t stop: it shifts into a steady operational rhythm.

Monthly. Automated revenue reports, transparent expense tracking, payout on the same day each month. If occupancy is trending lower than projected, you’ll know why and what we’re doing about it.

Per booking. Guest screening on every inquiry. Concierge coordination when guests want excursions, transfers, or stocking. Cleaning and inspection after every checkout.

Quarterly. Physical property check-ins. Maintenance recommendations before small issues become expensive ones. Seasonal pricing review to make sure you’re positioned correctly for what’s coming up on the calendar.

Year-round. Guest pipeline management across all platforms. Listing updates when new comparable properties enter the market. Tournament and event calendars factored into your pricing weeks in advance.

For a full breakdown of what we handle, see the Nest Stays owner services page. You may also want to read What Does a Vacation Rental Manager Actually Do? for a deeper look at the management side.


What Nest Stays Needs from You

Onboarding requires a few things from the owner’s side. This list is short: that’s the point.

  • Property access. Keys or access codes, HOA access if applicable, parking instructions.
  • Emergency contact. One person (you, a neighbor, a property contact in Costa Rica) we can reach if something requires an owner decision.
  • Owner blackout dates. When you want to use the property: log them before we go live, and update them whenever they change.
  • House rules. Any non-negotiables: no events, no pets, no smoking, minimum stay requirements. We build these into guest screening and listing policies.
  • Furniture and equipment inventory. A walkthrough or list of what’s in the property: appliances, furniture, anything we need to track for audit purposes.
  • Existing accounts. If you’re already listed on Airbnb or Vrbo, access to those accounts so we can migrate or rebuild your listings properly.

That’s it. Once we have these, we can run the property with minimal back-and-forth. Most owners check in monthly to read the report and occasionally to block personal dates. The rest we handle.


Timeline: First Call to First Booking

Here’s what the realistic calendar looks like:

WeekWhat Happens
Week 1Intro call + property assessment
Weeks 2–3Professional photography, listing creation, platform setup
Week 4Property goes live on Airbnb, Vrbo, Booking.com, and DirectStays
Weeks 6–8First booking for most new listings (varies by property and season)

A few variables that affect that last milestone: properties in Los Sueños or Jacó during high season (December–April) often book faster. Properties going live mid-green-season may take a few additional weeks to build their first reviews. Either way, the first booking isn’t the end goal. It’s the beginning of building a track record that compounds over time.


If you’re still evaluating whether professional management makes sense for your property, these guides can help:


The First Step

Most owners who reach out have been thinking about professional management for months: researching options, running income projections, wondering whether the commission is worth it.

The fastest way to answer those questions is a 30-minute call where you can ask them directly.

No commitment required. If it doesn’t make sense for your property, we’ll tell you. If it does, you’ll know what the next step looks like before the call ends.

Schedule your intro call at cal.com/neststays/intro →


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