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Short-term rentals in Portland

Local supply skews to Airbnb, with 2× the Booking.com inventory. Its largest professional operator, Sykes Holiday Cottages, runs 60 listings locally.

Explore the interactive Portland report

Data updated

Tracked listings
372
Market rank
#495 / 598
National share
under 0.1%
Professional operators
7

Listing mix by platform in Portland

Where the listings are in Portland

The dots are a representative sample of tracked short-term rentals — Airbnb in red, Booking.com in blue. Zoom and pan here, or open the full report for filters, operator overlays, and the listing-level view.

Airbnb Booking.com 250 sampled locations from 372 tracked listings — open the full interactive report

What the Portland short-term rental supply looks like

Listings by property type

How Portland's tracked listings split across property types on each platform.

  • Houses, cottages & holiday homes 253
  • Apartments & flats 61
  • Private & shared rooms 20
  • Hotels & hostels 17
  • B&Bs & guest houses 10
  • Unique & outdoor 10
  • Other 1

Listings by operator portfolio size

Tracked listings grouped by how many properties their operator runs — from single hosts to 26+ professionals.

  • Single listing 127
  • 2–5 listings 66
  • 6–25 listings 83
  • 26+ (professional) 96

Largest operators in Portland

Ranked by local tracked listings across Airbnb and Booking.com. Scores and portfolio review totals are aggregated across each operator's tracked United Kingdom listings. Together, the table and directory cover every professional operator we track in this market.

Scroll sideways to see all columns.

Largest operators in Portland, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 Sykes Holiday Cottages 60 4.67 / 5 8.9 / 10 131,996
2 Cottages.com 22 4.76 / 5 9.0 / 10 184,368
3 Holidaycottages.Co.Uk 7 4.73 / 5 8.9 / 10 35,230
4 53 Degrees Property 2 4.71 / 5 8.4 / 10 4,041
5 Jurassic Coast Holiday Homes 2 4.87 / 5 9.2 / 10 1,132
6 Oliver's Travels 2 4.81 / 5 — 31
7 Travelnest Ltd 1 4.38 / 5 8.1 / 10 47,351

All 7 professional operators in Portland

Browse the full United Kingdom operator directory →

Operators are indexed when they run at least 26 listings nationally and count Portland among their markets. See the full interactive Portland market report for the map, charts, and operator comparison.

How Portland compares

Portland ranks 495th of 598 tracked markets in the United Kingdom, with under 0.1% of national supply. Markets of similar size:

Photo credits

Browse the full United Kingdom city directory or the United Kingdom market report .

Portland market FAQ

How many short-term rentals are in Portland?

Portland has 372 tracked short-term rental listings as of 2026-06-07: 249 on Airbnb and 123 on Booking.com.

Who is the largest short-term rental operator in Portland?

The largest professional operator in Portland is Sykes Holiday Cottages, with 60 local listings.

Is Airbnb or Booking.com bigger in Portland?

Airbnb is bigger in Portland, with 249 listings against 123 on Booking.com.

How many professional operators run listings in Portland?

7 professional operators (26+ listings nationally) have a tracked presence in Portland. The full roster is listed on this page, and the interactive market report maps every listing.

About this data

Figures come from myDataValue's cross-platform market snapshot of 372 public short-term rental listings in Portland, matching Airbnb and Booking.com supply to the operators who run it. Operators shown have at least 26 listings on Airbnb or Booking.com nationally. Snapshot dates: Airbnb , Booking.com .

Spotted an inconsistency, or want fresher data for Portland? Report a data issue or request an update — corrections land with the next data refresh.