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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 61 listings locally.

Explore the interactive Portland report

Data updated

Tracked listings
371
Market rank
#493 / 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 and Booking.com in blue. Zoom and pan to explore the market, or open the full report for filters, operator overlays, and the listing-level view.

Airbnb Booking.com 250 sampled locations from 371 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 250
  • Apartments & flats 61
  • Private & shared rooms 20
  • Hotels & hostels 17
  • B&Bs & guest houses 11
  • Unique & outdoor 11
  • 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 122
  • 2–5 listings 77
  • 6–25 listings 78
  • 26+ (professional) 94

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 61 4.69 / 5 8.9 / 10 163,699
2 Cottages.com 20 4.77 / 5 9.0 / 10 213,860
3 holidaycottages.co.uk 7 4.73 / 5 8.9 / 10 75,737
4 53 Degrees Property 2 4.74 / 5 8.4 / 10 4,157
5 Jurassic Coast Holiday Homes 2 4.88 / 5 9.2 / 10 1,150
6 Oliver's Travels 2 4.86 / 5 10.0 / 10 697
7 Travelnest Ltd 1 4.53 / 5 8.1 / 10 83,730

All 7 professional operators in Portland

Local listings

Browse the full United Kingdom operator directory →

Operators enter the index after reaching 26 listings across the United Kingdom and count Portland among their markets. Published profile URLs remain stable across data refreshes. See the full interactive Portland market report for additional filters and operator comparisons.

How Portland compares

Portland ranks 493rd of 598 tracked markets in the United Kingdom, with under 0.1% of tracked supply in this coverage. 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 371 tracked short-term rental listings as of 2026-06-07: 248 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 61 local listings.

Is Airbnb or Booking.com bigger in Portland?

Airbnb is bigger in Portland, with 248 listings against 123 on Booking.com.

How many professional operators run listings in Portland?

7 indexed professional operators 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 371 public short-term rental listings in Portland, matching Airbnb and Booking.com supply to the operators who run it. Operators enter the index after reaching 26 listings on Airbnb or Booking.com across the United Kingdom. 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.