Insights from the 2025 Comparent 100 — and what scale actually means
In 2025, Comparent published its ranking of the top 100 vacation rental management companies in the United States.
Most readers treated it as a leaderboard.
We treated it as a segmentation dataset.
By isolating companies managing 250 listings or more, we can start answering a more useful question for investors, executives, and large operators:
What does “enterprise scale” actually look like in U.S. vacation rental management?
The answer is less uniform — and more instructive — than it appears at first glance.
Data source and scope
This article is based directly on the 2025 Comparent 100 dataset, which aggregates publicly available information on:
- portfolio size,
- headquarters location,
- markets served,
- founding year,
- guest and owner ratings (where available),
- team size (where disclosed),
- and qualitative descriptors (e.g. “legacy,” “tech-driven,” “urban,” “luxury”).
Comparent deserves full credit for compiling and publishing the dataset.
What follows is an interpretation of the 250+ listings segment, not a restatement of the ranking.
How large is “large” in U.S. vacation rentals?
Out of the 100 companies listed:
- 89 manage 250 or more listings
- Portfolio sizes range from ~250 to 37,437 listings
- The smallest company in the ranking manages 225 listings
- The largest listed portfolio is Casago (37,437 listings)
Within the 250+ segment, scale breaks down roughly as follows:
- Top 10: ~2,700 to 37,000+ listings
- #11–30: ~1,000 to 2,700 listings
- #31–50: ~500 to 1,000 listings
- #51–89: ~250 to 500 listings
For investors, this matters because “enterprise” in vacation rentals spans two full orders of magnitude — from regional operators with a few hundred homes to national platforms managing tens of thousands.
250 listings is a structural breakpoint
The reason 250 listings matters is not prestige — it’s complexity.
At roughly this scale:
- informal processes stop working,
- owner communication must be systematized,
- operations require layered management,
- and software becomes infrastructure, not tooling.
Below 250, growth is often founder-led.
Above 250, growth becomes organizational.
But organizational scale does not imply a single operating model.
One segment, multiple operating archetypes
Looking at named companies in the dataset, at least five distinct archetypes emerge among 250+ listing operators.
1. Legacy regional operators
These companies often predate Airbnb and grew through long-term owner relationships in a single destination.
Examples include:
- Twiddy & Company (Outer Banks, founded 1978)
- Southern Shores Realty (Outer Banks, founded 1954)
- Midgett Realty (Outer Banks, founded 1962)
- Surfside Realty Company (Myrtle Beach, founded 1962)
Typical traits:
- deep market density,
- strong local brands,
- slower geographic expansion,
- significant operational headcount.
Many manage 500–2,000+ listings within one or two adjacent markets.
2. Multi-market aggregators
These firms scale primarily through acquisition, franchising, or rapid multi-market rollout.
Examples include:
- Casago (listed at 37,437 listings)
- Grand Welcome
- VTrips
- Monarch (multiple subsidiaries)
The dataset highlights:
- companies with multiple subsidiaries (e.g. AwayDay, Monarch, VTrips),
- descriptors such as “multi-market” and “high-growth.”
Their advantage is speed of scale.
Their challenge is integration, consistency, and owner alignment across markets.
3. Tech-driven, multi-market platforms
These companies emphasize centralized systems and national reach.
Examples in the dataset include:
- Evolve — listed as operating across 99 markets, described as “tech-driven, multi-market,” with a reported team size of 800+
- AvantStay — listed across 96 markets, described as “high-growth,” with a reported team size of 501–1,000
They typically:
- operate across dozens of markets,
- centralize revenue, marketing, and support functions,
- rely heavily on software and standardized processes.
4. Luxury specialists
These firms scale selectively, prioritizing ADR and brand positioning over footprint.
Examples include:
- Nocturne Luxury Villas
- Home Team Luxury Rentals
- Red Rock Vacation Rentals
They often manage 250–1,000 listings, but with higher revenue per unit and tighter brand control.
From an investor perspective, these resemble premium hospitality brands more than platforms.
5. Urban and hybrid operators
These sit between short-term rentals, serviced apartments, and aparthotels.
Examples include:
- Kasa
- Placemakr
- Great Dwellings (Washington, DC)
They often:
- operate in fewer markets,
- manage fewer owners,
- and resemble hotel operators in structure and operations.
Headquarters still matter — even for national companies
A key clarification:
A company’s headquarters does not define where it operates.
Many firms in the dataset manage listings across multiple states.
However, headquarters still signal where a company was built and which market dynamics shaped its operating DNA.
In the Comparent data, headquarters cluster heavily in:
- Florida coastal markets,
- the Outer Banks (NC),
- Myrtle Beach (SC),
- the Smoky Mountains (NC/TN),
- mountain and ski destinations,
- and a smaller set of urban hubs.
These are mature vacation rental markets, where professional management developed early and owner relationships remain central.
Even national platforms often carry the imprint of the markets where they originated.
Size does not guarantee quality
Guest ratings across the 250+ segment range from 3.5 to 4.9+.
Owner ratings (available for a subset) vary even more:
- some large operators score near 5.0,
- others significantly lower.
The takeaway is simple:
Scale amplifies organizational design — good or bad.
At this level, execution, communication, and internal structure matter more than portfolio size alone.
Post-publication context (industry commentary)
The Comparent ranking reflects 2025 data.
Two major industry events that occurred shortly after publication are worth noting as context, not as part of the dataset itself.
Vacasa and Casago
Vacasa was acquired by Casago in 2025.
Since the acquisition, Casago has publicly communicated that it is divesting parts of Vacasa’s portfolio to local and regional property managers.
This suggests a redistribution of scale:
- Vacasa’s centralized footprint is fragmenting,
- new 500–2,000 listing operators are likely to emerge,
- rooted again in local markets.
Sonder
Sonder, which appears in the Comparent ranking and reported a team size of ~1,400, filed for bankruptcy in November 2025.
This outcome highlights the fragility of certain tech-forward, centralized models when market conditions tighten.
These developments are not part of the Comparent dataset, but they materially affect how the 250+ segment should be interpreted going forward.
What durable large operators tend to share
Across models, the most resilient large companies tend to exhibit:
- clear separation between execution and decision-making,
- disciplined owner communication,
- selective centralization,
- and leadership teams shaped by operations, not only growth.
They are operator-led and tech-enabled, rather than tech-led in isolation.
Why this matters for investors and executives
The Comparent 100 shows who reached scale.
What 2025 revealed is that:
- scale alone is not a moat,
- business model matters more than size,
- and market-rooted operators continue to compound.
For investors, the real question is not:
“Who is biggest?”
But:
“Which model of scale is this company pursuing — and what breaks first when conditions change?”
At 250+ listings, scale stops being a milestone.
It becomes a stress test.
Thibault Masson is a leading expert in vacation rental revenue management and dynamic pricing strategies. As Head of Product Marketing at PriceLabs and founder of Rental Scale-Up, Thibault empowers hosts and property managers with actionable insights and data-driven solutions. With over a decade managing luxury rentals in Bali and St. Barths, he is a sought-after industry speaker and prolific content creator, making complex topics simple for global audiences.
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